Search for "hydrogen peroxide" in Full Text gives 124 result(s) in Beilstein Journal of Organic Chemistry.
Beilstein J. Org. Chem. 2016, 12, 110–116, doi:10.3762/bjoc.12.12
Graphical Abstract
Scheme 1: Oxidation of SF5-anisole and phenol. 19F NMR yields are shown (isolated yields in parentheses).
Scheme 2: Proposed mechanism for the formation of 3 and 4 from SF5 aromatics 1 and 2.
Scheme 3: Oxidation of anisole 10 and phenol 11. 19F NMR yields are given.
Scheme 4: Synthesis of para-benzoquinone 12 and oxidation to maleic acid 4. 19F NMR yields are shown, in pare...
Scheme 5: Catalytic hydrogenation and Diels–Alder reaction of benzoquinone 12.
Figure 1: Optimized geometries of transition states of Diels–Alder reaction of cyclopentadiene with 12. Selec...
Scheme 6: Decomposition of 3 in water.
Scheme 7: Formation of acids 5, 18 and 19 from lactone 3.
Scheme 8: Synthesis of maleic anhydride 20 and Diels–Alder adducts 21.
Scheme 9: Reaction of maleic acid 4 with diazomethane.
Scheme 10: Decarboxylation of maleic acid 4 to acrylic acid 23 in DMSO and the preparation of deuterium labell...
Beilstein J. Org. Chem. 2016, 12, 50–72, doi:10.3762/bjoc.12.7
Graphical Abstract
Figure 1: Structures of α-, β- and γ-CD. Individual carbon atom numbering is shown for one D-glucopyranose su...
Figure 2: Associations of hydrophobic substituents (circled) (a) and their disruption through host–guest comp...
Figure 3: Decrease of aqueous solution viscosity at a shear rate of 50 s−1 due to α-CD (circles), β-CD (recta...
Figure 4: The effect of (a) α-CD, (b) β-CD and (c) γ-CD on the hydrophobic interactions between n-C18H37 subs...
Figure 5: The effect of SDS addition on viscosity shear rate dependence for 2 wt % aqueous PAAodn solutions c...
Figure 6: Host–guest complexation between polymers with cyclodextrin and hydrophobic substituents.
Figure 7: Variation of viscosity with mole ratio of CD substituents to hydrophobic substituents on poly(acryl...
Figure 8: Illustration of the competitive intermolecular host–guest complexation of either the adamantyl subs...
Figure 9: Competitive host–guest complexations in which either the adamantyl substituent (red) or the n-hexyl...
Figure 10: (a) Substituted chitosan in which acyl- and adamantyl-substitution is 5% and 12 %, respectively. (b...
Figure 11: The formation of a AD-PEG micelle followed by the formation of a AD-PEG/α-CD supramolecular hydroge...
Figure 12: Interaction of PEG-b-PAA block copolymer with cis-diamminedichloroplatinum(II), cisplatin, to form ...
Figure 13: Solution to hydrogel transitions (a)–(d) for a PAAddn segment in the presence of competitive photo-...
Figure 14: Structures of the poly(acrylate)-based polymers PAAAzo (trans), PAAAzo (cis), PAA3α-CD and PAA6α-CD...
Figure 15: Variation of viscosity of a PAA6α-CD/PAAAzo solution (circles) and a PAA3α-CD/PAAAzo solution (tria...
Figure 16: The structures proposed for the poly(ethylene glycol)-b-poly(ethylamine)-g-dextran·γ-CD, PEG-PEI-de...
Figure 17: Structure of poly(ethylene glycol) polyrotaxane with adamantyl end substituents, and its temperatur...
Figure 18: Copolymers of either (a) N,N-dimethylacrylamide (DMAA) or (b) N-isopropylacrylamine (NIPAAM) with 1...
Figure 19: The copolymer of isopropylacrylamine and methacrylated β-CD (a) and its complexation of the anions ...
Figure 20: Solution to hydrogel transitions for two segments of PAAddn in the presence of β-CD and change in t...
Figure 21: Preparation of a β-CD and adamantyl substituted acrylamide polymer hydrogel involving host–guest co...
Figure 22: Aqueous solutions of the polymers poly-β-CD and poly-α-BrNP form the poly-β-CD/poly-α-BrNP hydrogel ...
Figure 23: (a) Randomly β-CD substituted poly(acrylate), PAA-6β-CD. (b) Randomly ferrocenyl substituted poly(a...
Figure 24: (a) The β-CD, adamantyl and ferrocenyl substituted pAAm and pNiPAAM polymers. (b) The β-CD, adamant...
Beilstein J. Org. Chem. 2015, 11, 2549–2556, doi:10.3762/bjoc.11.275
Graphical Abstract
Figure 1: TPA (1), BPMEN (2) and (R,R′)-PDP (3) ligands.
Scheme 1: Allylic hydroxyamination of cyclohexene (7) using iron catalysts 4 and 5; i. 4 or 5 (10 mol %), Boc...
Scheme 2: Proposed mechanism for hydroxyamination of cyclohexene (7) by FeTPA (4) and FeBPMEN (5): (a) iron-m...
Scheme 3: Reaction of isoprene (14) under (a) Kirby’s conditions [54,55] and (b) FeTPA- or FeBPMEN-mediated hydoxyam...
Beilstein J. Org. Chem. 2015, 11, 1570–1582, doi:10.3762/bjoc.11.173
Graphical Abstract
Figure 1: Production and utilization of h+ and e– by photoactivation of a semiconductor.
Figure 2: Photoredox activity of TiO2 with moist air.
Scheme 1: TiO2 promoted oxidation of phenanthrene [29].
Scheme 2: SCPC assisted additions of allylic compounds to diazines and imines [40-42].
Scheme 3: TiO2 promoted addition and addition–cyclization reactions of tert-amines with electron-deficient al...
Scheme 4: Reactions of amines promoted by Pt-TiO2 [48,49].
Scheme 5: P25 Promoted alkylations of N-phenylmaleimide with diverse carboxylic acids [53,54]. aAccompanied by R–R d...
Scheme 6: SCPC cyclizations of aryloxyacetic acids with suitably sited alkene acceptors [54]. aYields in brackets...
Scheme 7: TiO2 promoted reactions of aryloxyacetic acids with maleic anhydride and maleimides [53,54].
Scheme 8: Photoredox addition–cyclization reactions of aryloxyacetic and related acids promoted by maleimide [63]....
Scheme 9: SCPC promoted homo-couplings and macrocyclizations with carboxylic acids [64].
Scheme 10: TiO2 promoted alkylations of alkenes with silanes [66] and thiols [67].
Scheme 11: TiO2 reduction of a nitrochromenone derivative [70].
Scheme 12: TiO2 mediated hydrodehalogenations and cyclizations of organic iodides [71].
Scheme 13: TiO2 promoted hydrogenations of maleimides, maleic anhydride and aromatic aldehydes [79].
Scheme 14: Mechanistic sketch of SCPC hydrogenation of aryl aldehydes.
Beilstein J. Org. Chem. 2015, 11, 1274–1331, doi:10.3762/bjoc.11.142
Graphical Abstract
Figure 1: General representation of cyclophanes.
Figure 2: cyclophanes one or more with heteroatom.
Figure 3: Metathesis catalysts 12–17 and C–C coupling catalyst 18.
Figure 4: Natural products containing the cyclophane skeleton.
Figure 5: Turriane family of natural products.
Scheme 1: Synthesis of [3]ferrocenophanes through Mannich reaction. Reagents and conditions: (i) excess HNMe2...
Scheme 2: Synthesis of cyclophanes through Michael addition. Reagents and conditions: (i) xylylene dibromide,...
Scheme 3: Synthesis of normuscopyridine analogue 37 through an oxymercuration–oxidation strategy. Reagents an...
Scheme 4: Synthesis of tribenzocyclotriyne 39 through Castro–Stephens coupling reaction. Reagents and conditi...
Scheme 5: Synthesis of cyclophane 43 through Glaser–Eglinton coupling. Reagents and conditions: (i) 9,10-bis(...
Scheme 6: Synthesis of the macrocyclic C-glycosyl cyclophane through Glaser coupling. Reagents and conditions...
Scheme 7: Synthesis of cyclophane-containing complex 49 through Glaser–Eglinton coupling reaction. Reagents a...
Scheme 8: Synthesis of cyclophane 53 through Glaser–Eglinton coupling. Reagents and conditions: (i) K2CO3, ac...
Figure 6: Cyclophanes 54–56 that have been synthesized through Glaser–Eglinton coupling.
Figure 7: Synthesis of tetrasubstituted [2.2]paracyclophane 57 and chiral cyclophyne 58 through Eglinton coup...
Scheme 9: Synthesis of cyclophane through Glaser–Hay coupling reaction. Reagents and conditions: (i) CuCl2 (1...
Scheme 10: Synthesis of seco-C/D ring analogs of ergot alkaloids through intramolecular Heck reaction. Reagent...
Scheme 11: Synthesis of muscopyridine 73 via Kumada coupling. Reagents and conditions: (i) 72, THF, ether, 20 ...
Scheme 12: Synthesis of the cyclophane 79 via McMurry coupling. Reagents and conditions: (i) 75, decaline, ref...
Scheme 13: Synthesis of stilbenophane 81 via McMurry coupling. Reagents and conditions: (i) TiCl4, Zn, pyridin...
Scheme 14: Synthesis of stilbenophane 85 via McMurry coupling. Reagents and conditions: (i) NBS (2 equiv), ben...
Figure 8: List of cyclophanes prepared via McMurry coupling reaction as a key step.
Scheme 15: Synthesis of paracyclophane by cross coupling involving Pd(0) catalyst. Reagents and conditions: (i...
Scheme 16: Synthesis of the cyclophane 112 via the pinacol coupling and 113 by RCM. Reagents and conditions: (...
Scheme 17: Synthesis of cyclophane derivatives 122a–c via Sonogoshira coupling. Reagents and conditions: (i) C...
Scheme 18: Synthesis of cyclophane 130 via Suzuki–Miyaura reaction as a key step. Reagents and conditions: (i)...
Scheme 19: Synthesis of the mycocyclosin via Suzuki–Miyaura cross coupling. Reagents and conditions: (i) benzy...
Scheme 20: Synthesis of cyclophanes via Wurtz coupling reaction Reagents and conditions: (i) PhLi, Et2O, C6H6,...
Scheme 21: Synthesis of non-natural glycophanes using alkyne metathesis. Reagents and conditions: (i) G-I (12)...
Figure 9: Synthesis of cyclophanes via ring-closing alkyne metathesis.
Scheme 22: Synthesis of crownophanes by cross-enyne metathesis. Reagents and conditions: (i) G-II (13), 5 mol ...
Scheme 23: Synthesis of (−)-cylindrocyclophanes A (156) and (−)-cylindrocyclophanes F (155). Reagents and cond...
Scheme 24: Synthesis of cyclophane 159 derivatives via SM cross-coupling and RCM. Reagents and conditions: (i)...
Scheme 25: Sexithiophene synthesis via cross metathesis. Reagents and conditions: (i) 161, Pd(PPh3)4, K2CO3, T...
Scheme 26: Synthesis of pyrrole-based cyclophane using enyne metathesis. Reagents and conditions: (i) Se, chlo...
Scheme 27: Synthesis of macrocyclic derivatives by RCM. Reagents and conditions: (i) G-I/G-II, CH2Cl2, 0.005 M...
Scheme 28: Synthesis of enantiopure β-lactam-based dienyl bis(dihydrofuran) 179. Reagents and conditions: (i) ...
Scheme 29: Synthesis of a [1.1.6]metaparacyclophane derivative 183 via SM cross coupling. Reagents and conditi...
Scheme 30: Synthesis of a [1.1.6]metaparacyclophane derivative 190 via SM cross coupling. Reagents and conditi...
Scheme 31: Template-promoted synthesis of cyclophanes involving RCM. Reagents and conditions: (i) acenaphthene...
Scheme 32: Synthesis of [3.4]cyclophane derivatives 200 via SM cross coupling and RCM. Reagents and conditions...
Figure 10: Examples for cyclophanes synthesized by RCM.
Scheme 33: Synthesis of the longithorone C framework assisted by fluorinated auxiliaries. Reagents and conditi...
Scheme 34: Synthesis of the longithorone framework via RCM. Reagents and conditions: (i) 213, NaH, THF, rt, 10...
Scheme 35: Synthesis of floresolide B via RCM as a key step. Reagents and conditions: (i) G-II (13, 0.1 equiv)...
Scheme 36: Synthesis of normuscopyridine (223) by the RCM strategy. Reagents and condition: (i) Mg, THF, hexen...
Scheme 37: Synthesis of muscopyridine (73) via RCM. Reagents and conditions: (i) 225, NaH, THF, 0 °C to rt, 1....
Scheme 38: Synthesis of muscopyridine (73) via RCM strategy. Reagents and conditions: (i) NaH, n-BuLi, 5-bromo...
Scheme 39: Synthesis of pyridinophane derivatives 223 and 245. Reagents and conditions: (i) PhSO2Na, TBAB, CH3...
Scheme 40: Synthesis of metacyclophane derivatives 251 and 253. Reagents and conditions: (i) 240, NaH, THF, rt...
Scheme 41: Synthesis of normuscopyridine and its higher analogues. Reagents and conditions: (i) alkenyl bromid...
Scheme 42: Synthesis of fluorinated ferrocenophane 263 via a [2 + 2] cycloaddition. Reagents and conditions: (...
Scheme 43: Synthesis of [2.n]metacyclophanes 270 via a [2 + 2] cycloaddition. Reagents and conditions: (i) Ac2...
Scheme 44: Synthesis of metacyclophane 273 by a [2 + 2 + 2] co-trimerization. Reagents and conditions: (i) [Rh...
Scheme 45: Synthesis of paracyclophane 276 via a [2 + 2 + 2] cycloaddition reaction. Reagents and conditions: ...
Scheme 46: Synthesis of cyclophane 278 via a [2 + 2 + 2] cycloaddition reaction. Reagents and conditions: (i) ...
Scheme 47: Synthesis of cyclophane 280 via a [2 + 2 + 2] cycloaddition. Reagents and conditions: (i) [(Rh(cod)(...
Scheme 48: Synthesis of taxane framework by a [2 + 2 + 2] cycloaddition. Reagents and conditions: (i) Cp(CO)2 ...
Scheme 49: Synthesis of cyclophane 284 and 285 via a [2 + 2 + 2] cycloaddition reaction. Reagents and conditio...
Scheme 50: Synthesis of pyridinophanes 293a,b and 294a,b via a [2 + 2 + 2] cycloaddition. Reagents and conditi...
Scheme 51: Synthesis of pyridinophanes 296 and 297 via a [2 + 2 + 2] cycloaddition. Reagents and conditions: (...
Scheme 52: Synthesis of triazolophane by a 1,3-dipolar cycloaddition. Reagents and conditions: (i) propargyl b...
Scheme 53: Synthesis of glycotriazolophane 309 by a click reaction. Reagents and conditions: (i) LiOH, H2O, Me...
Figure 11: Cyclophanes 310 and 311 prepared via click chemistry.
Scheme 54: Synthesis of cyclophane via the Dötz benzannulation. Reagents and conditions: (i) THF, 100 °C, 12 h...
Scheme 55: Synthesis of [6,6]metacyclophane by a Dötz benzannulation. Reagents and conditions: (i) THF, 100 °C...
Scheme 56: Synthesis of cyclophanes by a Dötz benzannulation. Reagents and conditions: (i) THF, 65 °C, 3 h; (i...
Scheme 57: Synthesis of muscopyridine (73) via an intramolecular DA reaction of ketene. Reagents and condition...
Scheme 58: Synthesis of bis[10]paracyclophane 336 via Diels–Alder reaction. Reagents and conditions: (i) DMAD,...
Scheme 59: Synthesis of [8]paracyclophane via DA reaction. Reagents and conditions: (i) maleic anhydride, 3–5 ...
Scheme 60: Biomimetic synthesis of (−)-longithorone A. Reagents and conditions: (i) Me2AlCl, CH2Cl2, −20 °C, 7...
Scheme 61: Synthesis of sporolide B (349) via a [4 + 2] cycloaddition reaction. Reagents and conditions: (i) P...
Scheme 62: Synthesis of the framework of (+)-cavicularin (352) via a [4 + 2] cycloaddition. Reagents and condi...
Scheme 63: Synthesis of oxazole-containing cyclophane 354 via Beckmann rearrangement. Reagents and conditions:...
Scheme 64: Synthesis of cyclophanes 360a–c via benzidine rearrangement. Reagents and conditions: (i) 356a–d, K2...
Scheme 65: Synthesis of cyclophanes 365a–c via benzidine rearrangement. Reagents and conditions: (i) BocNHNH2,...
Scheme 66: Synthesis of metacyclophane 367 via Ciamician–Dennstedt rearrangement. Reagents and conditions: (i)...
Scheme 67: Synthesis of cyclophane by tandem Claisen rearrangement and RCM as key steps. Reagents and conditio...
Scheme 68: Synthesis of cyclophane derivative 380. Reagents and conditions: (i) K2CO3, CH3CN, allyl bromide, r...
Scheme 69: Synthesis of metacyclophane via Cope rearrangement. Reagents and conditions: (i) MeOH, NaBH4, rt, 1...
Scheme 70: Synthesis of cyclopropanophane via Favorskii rearrangement. Reagents and conditions: (i) Br2, CH2Cl2...
Scheme 71: Cyclophane 389 synthesis via photo-Fries rearrangement. Reagents and conditions: (i) DMAP, EDCl/CHCl...
Scheme 72: Synthesis of normuscopyridine (223) via Schmidt rearrangement. Reagents and conditions: (i) ethyl s...
Scheme 73: Synthesis of crownophanes by tandem Claisen rearrangement. Reagents and conditions: (i) diamine, Et3...
Scheme 74: Attempted synthesis of cyclophanes via tandem Claisen rearrangement and RCM. Reagents and condition...
Scheme 75: Synthesis of muscopyridine via alkylation with 2,6-dimethylpyridine anion. Reagents and conditions:...
Scheme 76: Synthesis of cyclophane via Friedel–Craft acylation. Reagents and conditions: (i) CS2, AlCl3, 7 d, ...
Scheme 77: Pyridinophane 418 synthesis via Friedel–Craft acylation. Reagents and conditions: (i) 416, AlCl3, CH...
Scheme 78: Cyclophane synthesis involving the Kotha–Schölkopf reagent 421. Reagents and conditions: (i) NBS, A...
Scheme 79: Cyclophane synthesis involving the Kotha–Schölkopf reagent 421. Reagents and conditions: (i) BEMP, ...
Scheme 80: Cyclophane synthesis by coupling with TosMIC. Reagents and conditions: (i) (a) ClCH2OCH3, TiCl4, CS2...
Scheme 81: Synthesis of diaza[32]cyclophanes and triaza[33]cyclophanes. Reagents and conditions: (i) DMF, NaH,...
Scheme 82: Synthesis of cyclophane 439 via acyloin condensation. Reagents and conditions: (i) Na, xylene, 75%;...
Scheme 83: Synthesis of multibridged binuclear cyclophane 442 by aldol condensation. Reagents and conditions: ...
Scheme 84: Synthesis of various macrolactones. Reagents and conditions: (i) iPr2EtN, DMF, 77–83%; (ii) TBDMSCl...
Scheme 85: Synthesis of muscone and muscopyridine via Yamaguchi esterification. Reagents and conditions: (i) 4...
Scheme 86: Synthesis of [5]metacyclophane via a double elimination reaction. Reagents and conditions: (i) LiBr...
Figure 12: Cyclophanes 466–472 synthesized via Hofmann elimination.
Scheme 87: Synthesis of cryptophane via Baylis–Hillman reaction. Reagents and conditions: (i) methyl acrylate,...
Scheme 88: Synthesis of cyclophane 479 via double Chichibabin reaction. Reagents and conditions: (i) excess 478...
Scheme 89: Synthesis of cyclophane 483 via double Chichibabin reaction. Reagents and conditions: (i) 481, OH−;...
Scheme 90: Synthesis of cyclopeptide via an intramolecular SNAr reaction. Reagents and conditions: (i) TBAF, T...
Scheme 91: Synthesis of muscopyridine (73) via C-zip ring enlargement reaction. Reagents and conditions: (i) H...
Figure 13: Mechanism of the formation of compound 494.
Scheme 92: Synthesis of indolophanetetraynes 501a,b using the Nicholas reaction as a key step. Reagents and co...
Scheme 93: Synthesis of cyclophane via radical cyclization. Reagents and conditions: (i) cyclododecanone, phen...
Scheme 94: Synthesis of (−)-cylindrocyclophanes A (156) and (−)-cylindrocyclophanes F (155). Reagents and cond...
Scheme 95: Cyclophane synthesis via Wittig reaction. Reagents and conditions: (i) LiOEt (2.1 equiv), THF, −78 ...
Figure 14: Representative examples of cyclophanes synthesized via Wittig reaction.
Scheme 96: Synthesis of the [6]paracyclophane via isomerization of Dewar benzene. Reagents and conditions: (i)...
Beilstein J. Org. Chem. 2015, 11, 1175–1186, doi:10.3762/bjoc.11.132
Graphical Abstract
Figure 1: Structure of Eriochrome Blue Black B.
Scheme 1: Cyclopalladation reactions of (S)-4-isopropyl-2-(naphthalen-1-yl)oxazoline.
Scheme 2: Synthesis of cyclopalladated complex from bis-oxazoline.
Figure 2: ORTEP drawing of the complex 8.
Scheme 3: Synthesis of the bis(oxazoline) coordinated complexes.
Figure 3: ORTEP drawing of the complex 9.
Figure 4: Change in color removal in the presence of different catalysts within 10 min (before filtration). T...
Figure 5: Change in color removal in the presence of different catalysts (after filtration over 10 min).
Figure 6: Evolution of the color degradation against time using Eriochrome plus H2O2, the complex plus H2O2 o...
Figure 7: Change of the concentration of the Erio solution with the variation of H2O2 dose.
Figure 8: Evolution of the color removal against initial dye concentration.
Figure 9: Change of the color removal versus temperature.
Figure 10: Recycling experiments for Erio removal (C0 = 30 ppm, 20 mL) in the presence of catalyst 9 at pH 7 a...
Scheme 4: Proposed mechanism of decolorization.
Beilstein J. Org. Chem. 2015, 11, 980–993, doi:10.3762/bjoc.11.110
Graphical Abstract
Figure 1: PV-PTFE reaction design.
Figure 2: Solvent uptake in the delivery of bromine into dichloromethane (a) 0 min, (b) 0.50 min, (c) 0.83 mi...
Figure 3: Solvent column heights of bromine delivery into dichloromethane (○) and ethyl acetate. (♦).
Figure 4: Reproducibility of bromine delivery into a) dichloromethane and b) ethyl acetate. In each case thre...
Figure 5: Height of the solvent column in the course of the bromination of cyclohexene in (a) dichloromethane...
Figure 6: Height of the solvent column in the course of the bromination of cyclohexene in ethyl acetate (♦) a...
Figure 7: Solvent uptake when the delivery tube is inserted to a shallow depth. The solvent uptake stopped on...
Scheme 1: Iodolactonization of unsaturated diester 1 with iodine monochloride in dichlormethane.
Figure 8: (a) The delivery tube is immersed into the solution and there is a considerable solvent uptake. (b)...
Figure 9: Transport of dyed dimethyl phthalate in dichloromethane after (a) 0 h, (b) 1 h, (c) 2 h, (d) 3 h an...
Figure 10: Transport of dyed dimethyl phthalate in ethyl acetate after (a) 0 h, (b) 0.17 h, (c) 1 h, (d) 3 h, ...
Scheme 2: Chemiluminescence reaction of diaryl oxalate esters oxidized by hydrogen peroxide in the presence o...
Figure 11: When the diaryl oxalate was oxidized by aqueous peroxide solution, chemiluminescence was observed o...
Figure 12: Progression of PV-PTFE chemiluminescence with aqueous peroxide solution in the vial after (a) 10 mi...
Figure 13: Progression of PV-PTFE chemiluminescence with acetonitrile–aqueous peroxide solution in the vial af...
Figure 14: Diffusion of dimethyl phthalate assisted by tert-butanol through PTFE was visualized in a chemilumi...
Figure 15: Corrosion of aluminum resulting from bromine applied directly to metal.
Figure 16: Discoloration of aluminum from bromine applied to PTFE tape on metal.
Figure 17: After stirring bars were cut open, some iron bars were found to be corroded.
Figure 18: (a) Diffusion of bromine through a bulk PTFE from stirring bar into dichloromethane after 2 h. (b) ...
Figure 19: Diffusion of bromine through a PTFE tube.
Figure 20:
(a) The reaction of benzene and bromine in the absence of a stirring bar (), in the presence of a n...
Beilstein J. Org. Chem. 2015, 11, 392–402, doi:10.3762/bjoc.11.45
Graphical Abstract
Figure 1: Preferential sites of cholesterol electrooxidation.
Scheme 1: Functionalization of the cholesterol side chain.
Scheme 2: Oxidation of cholestane-3β,5α,6β-triol triacetate (3) with the Gif system.
Scheme 3: Electrochemical oxidation of cholesteryl acetate (1a) with dioxygen and iron–picolinate complexes.
Scheme 4: Electrochemical chlorination of cholesterol catalyzed by FeCl3.
Scheme 5: Electrochemical chlorination of Δ5-steroids.
Scheme 6: Electrochemical bromination of Δ5-steroids in different solvents.
Scheme 7: Direct electrochemical acetoxylation of cholesterol at the allylic position.
Scheme 8: Direct anodic oxidation of cholesterol in dichloromethane.
Scheme 9: A plausible mechanism of the electrochemical oxidation of cholesterol in dichloromethane.
Scheme 10: The electrochemical formation of glycosides and glycoconjugates.
Scheme 11: Efficient electrochemical oxidation of cholesterol to cholesta-4,6-dien-3-one (24).
Beilstein J. Org. Chem. 2015, 11, 265–270, doi:10.3762/bjoc.11.29
Graphical Abstract
Figure 1: Hyperaspidinols A (1) and B (2) and other compounds 3-6 from Hypericum chinense.
Figure 2: Hyperaspidinol A (1), target compound 7 and proposed precursors.
Scheme 1: Reagents and conditions: (i) triethylphosphonoacetate, DBU, THF, 48 h, 94%; (ii) H2, 10% Pd/C, EtOA...
Scheme 2: Reagents and conditions: (i) H3C(CH3O)NH·HCl, n-BuLi, THF, −78 °C, 4 h, 81%; (ii) 1-bromo-3,4-methy...
Figure 3: NOESY correlations in isomers 7a and 7b.
Figure 4: 3D representation of 7a.
Figure 5: 3D representation of 7b.
Figure 6: Possible mechanism for the formation of furo[2,3-b]chromenes 7a and 7b.
Beilstein J. Org. Chem. 2015, 11, 92–146, doi:10.3762/bjoc.11.13
Graphical Abstract
Scheme 1: Cross-dehydrogenative coupling.
Scheme 2: Cross-dehydrogenative C–O coupling.
Scheme 3: Regioselective ortho-acetoxylation of meta-substituted arylpyridines and N-arylamides.
Scheme 4: ortho-Acyloxylation and alkoxylation of arenes directed by pyrimidine, benzoxazole, benzimidazole a...
Scheme 5: Cu(OAc)2/AgOTf/O2 oxidative system in the ortho-alkoxylation of arenes.
Scheme 6: Pd(OAc)2/persulfate oxidative system in the ortho-alkoxylation and acetoxylation of arenes with nit...
Scheme 7: ortho-Acetoxylation and methoxylation of O-methyl aryl oximes, N-phenylpyrrolidin-2-one, and (3-ben...
Scheme 8: Ruthenium-catalyzed ortho-acyloxylation of acetanilides.
Scheme 9: Acetoxylation and alkoxylation of arenes with amide directing group using Pd(OAc)2/PhI(OAc)2 oxidat...
Scheme 10: Alkoxylation of azoarenes, 2-aryloxypyridines, picolinamides, and N-(1-methyl-1-(pyridin-2-yl)ethyl...
Scheme 11: Acetoxylation of compounds containing picolinamide and quinoline-8-amine moieties using the Pd(OAc)2...
Scheme 12: (CuOH)2CO3 catalyzed oxidative ortho-etherification using air as oxidant.
Scheme 13: Copper-catalyzed aerobic alkoxylation and aryloxylation of arenes containing pyridine-N-oxide moiet...
Scheme 14: Cobalt-catalyzed aerobic alkoxylation of arenes and alkenes containing pyridine N-oxide moiety.
Scheme 15: Non-symmetric double-fold C–H ortho-acyloxylation.
Scheme 16: N-nitroso directed ortho-alkoxylation of arenes.
Scheme 17: Selective alkoxylation and acetoxylation of alkyl groups.
Scheme 18: Acetoxylation of 2-alkylpyridines and related compounds.
Scheme 19: Acyloxylation and alkoxylation of alkyl fragments of substrates containing amide or sulfoximine dir...
Scheme 20: Palladium-catalyzed double sp3 C–H alkoxylation of N-(quinolin-8-yl)amides for the synthesis of sym...
Scheme 21: Copper-catalyzed acyloxylation of methyl groups of N-(quinolin-8-yl)amides.
Scheme 22: One-pot acylation and sp3 C–H acetoxylation of oximes.
Scheme 23: Possible mechanism of oxidative esterification catalyzed by N-heterocyclic nucleophilic carbene.
Scheme 24: Oxidative esterification employing stoichiometric amounts of aldehydes and alcohols.
Scheme 25: Selective oxidative coupling of aldehydes with alcohols in the presence of amines.
Scheme 26: Iodine mediated oxidative esterification.
Scheme 27: Oxidative C–O coupling of benzyl alcohols with methylarenes under the action of Bu4NI/t-BuOOH syste...
Scheme 28: Oxidative coupling of methyl- and ethylarenes with aromatic aldehydes under the action of Bu4NI/t-B...
Scheme 29: Cross-dehydrogenative C–O coupling of aldehydes with t-BuOOH in the presence of Bu4NI.
Scheme 30: Bu4NI-catalyzed α-acyloxylation reaction of ethers and ketones with aldehydes and t-BuOOH.
Scheme 31: Oxidative coupling of aldehydes with N-hydroxyimides and hexafluoroisopropanol.
Scheme 32: Oxidative coupling of alcohols with N-hydroxyimides.
Scheme 33: Oxidative coupling of aldehydes and primary alcohols with N-hydroxyimides using (diacetoxyiodo)benz...
Scheme 34: Proposed mechanism of the oxidative coupling of aldehydes and N-hydroxysuccinimide under action of ...
Scheme 35: Oxidative coupling of aldehydes with pivalic acid (172).
Scheme 36: Oxidative C–O coupling of aldehydes with alkylarenes using the Cu(OAc)2/t-BuOOH system.
Scheme 37: Copper-catalyzed acyloxylation of C(sp3)-H bond adjacent to oxygen in ethers using benzyl alcohols.
Scheme 38: Oxidative C–O coupling of aromatic aldehydes with cycloalkanes.
Scheme 39: Ruthenium catalyzed cross-dehydrogenative coupling of primary and secondary alcohols.
Scheme 40: Cross-dehydrogenative C–O coupling reactions of β-dicarbonyl compounds with sulfonic acids, acetic ...
Scheme 41: Acyloxylation of ketones, aldehydes and β-dicarbonyl compounds using carboxylic acids and Bu4NI/t-B...
Scheme 42: Acyloxylation of ketones using Bu4NI/t-BuOOH system.
Scheme 43: Cross-dehydrogenative C–O coupling of β-dicarbonyl compounds and their heteroanalogues with N-hydro...
Scheme 44: Cross-dehydrogenative C–O coupling of β-dicarbonyl compounds and their heteroanalogues with t-BuOOH....
Scheme 45: Oxidative C–O coupling of 2,6-dialkylphenyl-β-keto esters and thioesters with tert-butyl hydroxycar...
Scheme 46: α’-Acyloxylation of α,β-unsaturated ketones using KMnO4.
Scheme 47: Possible mechanisms of the acetoxylation at the allylic position of alkenes by Pd(OAc)2.
Scheme 48: Products of the oxidation of terminal alkenes by Pd(II)/AcOH/oxidant system.
Scheme 49: Acyloxylation of terminal alkenes with carboxylic acids.
Scheme 50: Synthesis of linear E-allyl esters by cross-dehydrogenative coupling of terminal alkenes wih carbox...
Scheme 51: Pd(OAc)2-catalyzed acetoxylation of Z-vinyl(triethylsilanes).
Scheme 52: α’-Acetoxylation of α-acetoxyalkenes with copper(II) chloride in acetic acid.
Scheme 53: Oxidative acyloxylation at the allylic position of alkenes and at the benzylic position of alkylare...
Scheme 54: Copper-catalyzed alkoxylation of methylheterocyclic compounds using di-tert-butylperoxide as oxidan...
Scheme 55: Oxidative C–O coupling of methylarenes with β-dicarbonyl compounds or phenols.
Scheme 56: Copper-catalyzed esterification of methylbenzenes with cyclic ethers and cycloalkanes.
Scheme 57: Oxidative C–O coupling of carboxylic acids with toluene catalyzed by Pd(OAc)2.
Scheme 58: Oxidative acyloxylation at the allylic position of alkenes with carboxylic acids using the Bu4NI/t-...
Scheme 59: Cross-dehydrogenative C–O coupling of carboxylic acids with alkylarenes using the Bu4NI/t-BuOOH sys...
Scheme 60: Oxidative C–O cross-coupling of methylarenes with ethyl or isopropylarenes.
Scheme 61: Phosphorylation of benzyl C–H bonds using the Bu4NI/t-BuOOH oxidative system.
Scheme 62: Selective C–H acetoxylation of 2,3-disubstituted indoles.
Scheme 63: Acetoxylation of benzylic position of alkylarenes using DDQ as oxidant.
Scheme 64: C–H acyloxylation of diarylmethanes, 3-phenyl-2-propen-1-yl acetate and dimethoxyarene using DDQ.
Scheme 65: Cross-dehydrogenative C–O coupling of 1,3-diarylpropylenes and 1,3-diarylpropynes with alcohols.
Scheme 66: One-pot azidation and C–H acyloxylation of 3-chloro-1-arylpropynes.
Scheme 67: Cross-dehydrogenative C–O coupling of 1,3-diarylpropylenes, (E)-1-phenyl-2-isopropylethylene and is...
Scheme 68: Cross-dehydrogenative C–O coupling of alkylarenes and related compounds with N-hydroxyphthalimide.
Scheme 69: Acetoxylation at the benzylic position of alkylarenes mediated by N-hydroxyphthalimide.
Scheme 70: C–O coupling of methylarenes with aromatic carboxylic acids employing the NaBrO3/NaHSO3 system.
Scheme 71: tert-Butyl peroxidation of allyl, propargyl and benzyl ethers catalyzed by Fe(acac)3.
Scheme 72: Cross-dehydrogenative C–O coupling of ethers with carboxylic acids mediated by Bu4NI/t-BuOOH system....
Scheme 73: Oxidative acyloxylation of dimethylamides and dioxane with 2-aryl-2-oxoacetic acids accompanied by ...
Scheme 74: tert-Butyl peroxidation of N-benzylamides and N-allylbenzamide using the Bu4NI/t-BuOOH system.
Scheme 75: Cross-dehydrogenative C–O coupling of aromatic carboxylic acids with ethers using Fe(acac)3 as cata...
Scheme 76: Cross-dehydrogenative C–O coupling of cyclic ethers with 2-hydroxybenzaldehydes using iron carbonyl...
Scheme 77: Cross-dehydrogenative C–O coupling of ethers with β-dicarbonyl compounds and phenols using copper c...
Scheme 78: Cross-dehydrogenative C–O coupling of 2-hydroxybenzaldehyde with dioxane catalyzed by Cu2(BPDC)2(BP...
Scheme 79: Ruthenium chloride-catalyzed acyloxylation of β-lactams.
Scheme 80: Ruthenium-catalyzed tert-butyl peroxydation amides and acetoxylation of β-lactams.
Scheme 81: PhI(OAc)2-mediated α,β-diacetoxylation of tertiary amines.
Scheme 82: Electrochemical oxidative methoxylation of tertiary amines.
Scheme 83: Cross-dehydrogenative C–O coupling of ketene dithioacetals with carboxylic acids in the presence of...
Scheme 84: Cross-dehydrogenative C–O coupling of enamides with carboxylic acids using iodosobenzene as oxidant....
Scheme 85: Oxidative alkoxylation, acetoxylation, and tosyloxylation of acylanilides using PhI(O(O)CCF3)2 in t...
Scheme 86: Proposed mechanism of the oxidative C–O coupling of actetanilide with O-nucleophiles in the presenc...
Scheme 87: Three-component coupling of aldehydes, anilines and alcohols involving oxidative intermolecular C–O...
Scheme 88: Oxidative coupling of phenols with alcohols.
Scheme 89: 2-Acyloxylation of quinoline N-oxides with arylaldehydes in the presence of the CuOTf/t-BuOOH syste...
Scheme 90: Cross-dehydrogenative C–O coupling of azoles with primary alcohols.
Scheme 91: Oxidation of dipyrroles to dipyrrins and subsequent oxidative alkoxylation in the presence of Na3Co...
Scheme 92: Oxidative dehydrogenative carboxylation of alkanes and cycloalkanes to allylic esters.
Scheme 93: Pd-catalyzed acetoxylation of benzene.
Beilstein J. Org. Chem. 2014, 10, 2594–2602, doi:10.3762/bjoc.10.272
Graphical Abstract
Figure 1: Pharmacologically active derivatives 1–4 containing the 1,4-benzoxazepine moiety or its analogue.
Scheme 1: Domino Knoevenagel–[1,5]-hydride shift cyclization reaction for the preparation of condensed 1,4-be...
Scheme 2: i) a) NaN3, CF3COOH, b) H2O, Δ (77%); ii) LiAlH4, dry THF, Δ (80%); iii) 11b, K2CO3, toluene, Δ (71...
Figure 2: Lowest-energy conformers of a) trans-(2S,15aS)-7a (>99.9%) with the replacement of the N-methyl gro...
Figure 3: Lowest-energy conformers of a) cis-(2R,15aS)-7a (99.4%) with the replacement of the N-methyl groups...
Figure 4: HPLC-ECD spectra of the first-eluting (black curve) and second-eluting (red curve) enantiomers of a...
Figure 5: Protective effect of compound 7a on hydrogen peroxide-induced neurotoxicity in SH-SY5Y cells. ##P <...
Figure 6: Protective effect of compound 7b on β-amyloid25–35-induced neurotoxicity in SH-SY5Y cells. ##P < 0....
Beilstein J. Org. Chem. 2014, 10, 2361–2366, doi:10.3762/bjoc.10.246
Graphical Abstract
Scheme 1: Oligomerization of N-(4-hydroxyphenyl)mandelamide (1).
Figure 1: 2D ROESY NMR spectrum (600 MHz, D2O) of the racemate 1 complexed with RAMEB-CD.
Figure 2: MALDI–TOF MS spectrum of the oligomers synthesized with laccase from the racemate 1.
Beilstein J. Org. Chem. 2014, 10, 1267–1271, doi:10.3762/bjoc.10.127
Graphical Abstract
Scheme 1: General transformation of selenides to selenones.
Scheme 2: Phenylselenone 2 as useful leaving group for the synthesis of different organic molecules.
Beilstein J. Org. Chem. 2014, 10, 921–928, doi:10.3762/bjoc.10.90
Graphical Abstract
Scheme 1: Aliphatic peracid mediated bromination of aminoanthracene-9,10-dinone.
Scheme 2: Plausible mechanism for the bromination of aminoanthracene-9,10-dione [36,37].
Beilstein J. Org. Chem. 2014, 10, 680–691, doi:10.3762/bjoc.10.61
Graphical Abstract
Scheme 1: Synthetic route for the synthesis of thiol functionalized 4-alkylphenols.
Scheme 2: Synthetic route for the chain transfer polymerization of N,N-diethylacrylamide (7) with CTA 6a and ...
Figure 1: Section of the MALDI –TOF spectrum of polymer 8b, indicating the high degree of end-group functiona...
Figure 2: 1H NMR spectrum of polymer 9b in CDCl3 (300 MHz, rt).
Figure 3: Top left: Section of the FTIR-spectrum of polymer 8b (black line) in comparison to 8bOx (red line);...
Figure 4: Dependency of the cloud point values on the degree of polymerization (calculated by end-group analy...
Figure 5: Shifts of the cloud points after the oxidation of the polymers (8a–d, 9a–d) to its corresponding su...
Figure 6: Turbidimetry measurements of polymer 8b (straight black line – heating curve; dotted black line – c...
Figure 7: 2D NMR NOESY spectrum of polymer 8b with two equivalents RAMEB-CD in D2O (600 MHz, rt).
Figure 8: Left: Schematic illustration of the micellar-like structures and reversibility by addition of RAMEB...
Figure 9: Schematic illustration of the micellar-like structures, its deformation upon addition of one equiva...
Beilstein J. Org. Chem. 2014, 10, 237–250, doi:10.3762/bjoc.10.19
Graphical Abstract
Scheme 1: 1-Boron-substituted 1,3-diene in a tandem cycloaddition [4 + 2]/allylboration sequence.
Scheme 2: Lewis acid catalyst in the tandem cycloaddition [4 + 2]/allylboration sequence.
Scheme 3: Synthesis of an advanced precursor of clerodin.
Scheme 4: Intramolecular Diels–Alder/allylboration sequence.
Scheme 5: Diastereoselective Diels–Alder reaction with N-phenylmaleimide and 4-phenyltriazoline-3,5-dione.
Scheme 6: Asymmetric synthesis of a α-hydroxyalkylcyclohexane.
Scheme 7: Tandem [4 + 2]-cycloaddition/allylboration of 3-silyloxy- and 4-alkoxy-dienyl boronates.
Scheme 8: Metal-mediated cycloisomerization/Diels–Alder reaction/allylboration sequence.
Scheme 9: Cobalt-catalyzed Diels–Alder/allylboration sequence.
Scheme 10: A two-step reaction sequence for the synthesis of tetrahydronaphthalenes 12.
Scheme 11: Tandem sequence based on the Petasis borono–Mannich reaction as first key step.
Scheme 12: One-pot tandem dimerization/allylboration reaction of 1,3-diene-2-boronate.
Scheme 13: Tandem Diels–Alder/cross-coupling reactions of trifluoroborates 15.
Scheme 14: Diels–Alder/cross-coupling reactions of 16.
Scheme 15: Metal catalyzed tandem Diels–Alder/hydrolysis reactions.
Scheme 16: Synthesis of anti-1,5-diols 18 by triple aldehyde addition.
Scheme 17: Catalytic enantioselective three-component hetero-[4 + 2]-cycloaddition/allylboration sequence.
Scheme 18: Synthesis of natural products using the catalytic enantioselective HDA/allylboration sequence.
Scheme 19: Total synthesis of a thiomarinol derivative.
Scheme 20: Synthesis of an advanced intermediate 27 for the east fragment of palmerolide A.
Scheme 21: Bicyclic piperidines from tandem aza-[4 + 2]-cycloaddition/allylboration.
Scheme 22: Hydrogenolysis reactions of hydrazinopiperidines.
Scheme 23: Tandem aza-[4 + 2]-cycloaddition/allylboration/retrosulfinyl-ene sequence.
Scheme 24: Boronated heterodendralene 32 in [4 + 2]-cycloadditions.
Scheme 25: Synthesis of tricyclic imides derivatives.
Scheme 26: Synthesis of 37 via a HDA/allylboration/DA sequence.
Scheme 27: Diels–Alder/allylboration sequence.
Beilstein J. Org. Chem. 2014, 10, 155–162, doi:10.3762/bjoc.10.13
Graphical Abstract
Figure 1: Structures of dimebon and SS peptides.
Scheme 1: Synthesis of starting N-substituted tetrahydro-γ-carbolines 3a–d.
Scheme 2: Synthesis of peptides 5 through the Ugi reaction.
Scheme 3: Synthesis of N-substituted tetrahydro-γ-carbolines containing protected peptide residues.
Scheme 4: Synthesis of dihydrochloride salts 7a–g.
Beilstein J. Org. Chem. 2014, 10, 34–114, doi:10.3762/bjoc.10.6
Graphical Abstract
Figure 1: Five and six-membered cyclic peroxides.
Figure 2: Artemisinin and semi-synthetic derivatives.
Scheme 1: Synthesis of 3-hydroxy-1,2-dioxolanes 3a–c.
Scheme 2: Synthesis of dioxolane 6.
Scheme 3: Photooxygenation of oxazolidines 7a–d with formation of spiro-fused oxazolidine-containing dioxolan...
Scheme 4: Oxidation of cyclopropanes 10a–e and 11a–e with preparation of 1,2-dioxolanes 12a–e.
Scheme 5: VO(acac)2-catalyzed oxidation of silylated bicycloalkanols 13a–c.
Scheme 6: Mn(II)-catalyzed oxidation of cyclopropanols 15a–g.
Scheme 7: Oxidation of aminocyclopropanes 20a–c.
Scheme 8: Synthesis of aminodioxolanes 24.
Figure 3: Trifluoromethyl-containing dioxolane 25.
Scheme 9: Synthesis of 1,2-dioxolanes 27a–e by the oxidation of cyclopropanes 26a–e.
Scheme 10: Photoinduced oxidation of methylenecyclopropanes 28.
Scheme 11: Irradiation-mediated oxidation.
Scheme 12: Application of diazene 34 for dioxolane synthesis.
Scheme 13: Mn(OAc)3-catalyzed cooxidation of arylacetylenes 37a–h and acetylacetone with atmospheric oxygen.
Scheme 14: Peroxidation of (2-vinylcyclopropyl)benzene (40).
Scheme 15: Peroxidation of 1,4-dienes 43a,b.
Scheme 16: Peroxidation of 1,5-dienes 46.
Scheme 17: Peroxidation of oxetanes 53a,b.
Scheme 18: Peroxidation of 1,6-diene 56.
Scheme 19: Synthesis of 3-alkoxy-1,2-dioxolanes 62a,b.
Scheme 20: Synthesis of spiro-bis(1,2-dioxolane) 66.
Scheme 21: Synthesis of dispiro-1,2-dioxolanes 68, 70, 71.
Scheme 22: Synthesis of spirohydroperoxydioxolanes 75a,b.
Scheme 23: Synthesis of spirohydroperoxydioxolane 77 and dihydroperoxydioxolane 79.
Scheme 24: Ozonolysis of azepino[4,5-b]indole 80.
Scheme 25: SnCl4-mediated fragmentation of ozonides 84a–l in the presence of allyltrimethylsilane.
Scheme 26: SnCl4-mediated fragmentation of bicyclic ozonide 84m in the presence of allyltrimethylsilane.
Scheme 27: MCl4-mediated fragmentation of alkoxyhydroperoxides 96 in the presence of allyltrimethylsilane.
Scheme 28: SnCl4-catalyzed reaction of monotriethylsilylperoxyacetal 108 with alkene 109.
Scheme 29: SnCl4-catalyzed reaction of triethylsilylperoxyacetals 111 with alkenes.
Scheme 30: Desilylation of tert-butyldimethylsilylperoxy ketones 131a,b followed by cyclization.
Scheme 31: Deprotection of peroxide 133 followed by cyclization.
Scheme 32: Asymmetric peroxidation of methyl vinyl ketones 137a–e.
Scheme 33: Et2NH-catalyzed intramolecular cyclization.
Scheme 34: Synthesis of oxodioxolanes 143a–j.
Scheme 35: Haloperoxidation accompanied by intramolecular ring closure.
Scheme 36: Oxidation of triterpenes 149a–d with Na2Cr2O7/N-hydroxysuccinimide.
Scheme 37: Curtius and Wolff rearrangements to form 1,2-dioxolane ring-retaining products.
Scheme 38: Oxidative desilylation of peroxide 124.
Scheme 39: Synthesis of dioxolane 158, a compound containing the aminoquinoline antimalarial pharmacophore.
Scheme 40: Diastereomers of plakinic acid A, 162a and 162b.
Scheme 41: Ozonolysis of alkenes.
Scheme 42: Cross-ozonolysis of alkenes 166 with carbonyl compounds.
Scheme 43: Ozonolysis of the bicyclic cyclohexenone 168.
Scheme 44: Cross-ozonolysis of enol ethers 172a,b with cyclohexanone.
Scheme 45: Griesbaum co-ozonolysis.
Scheme 46: Reactions of aryloxiranes 177a,b with oxygen.
Scheme 47: Intramolecular formation of 1,2,4-trioxolane 180.
Scheme 48: Formation of 1,2,4-trioxolane 180 by the reaction of 1,5-ketoacetal 181 with H2O2.
Scheme 49: 1,2,4-Trioxolane 186 with tetrazole fragment.
Scheme 50: 1,2,4-Trioxolane 188 with a pyridine fragment.
Scheme 51: 1,2,4-Trioxolane 189 with pyrimidine fragment.
Scheme 52: Synthesis of aminoquinoline-containing 1,2,4-trioxalane 191.
Scheme 53: Synthesis of arterolane.
Scheme 54: Oxidation of diarylheptadienes 197a–c with singlet oxygen.
Scheme 55: Synthesis of hexacyclinol peroxide 200.
Scheme 56: Oxidation of enone 201 and enenitrile 203 with singlet oxygen.
Scheme 57: Synthesis of 1,2-dioxanes 207 by oxidative coupling of carbonyl compounds 206 and alkenes 205.
Scheme 58: 1,2-Dioxanes 209 synthesis by co-oxidation of 1,5-dienes 208 and thiols.
Scheme 59: Synthesis of bicyclic 1,2-dioxanes 212 with aryl substituents.
Scheme 60: Isayama–Mukaiyama peroxysilylation of 1,5-dienes 213 followed by desilylation under acidic conditio...
Scheme 61: Synthesis of bicycle 218 with an 1,2-dioxane ring.
Scheme 62: Intramolecular cyclization with an oxirane-ring opening.
Scheme 63: Inramolecular cyclization with the oxetane-ring opening.
Scheme 64: Intramolecular cyclization with the attack on a keto group.
Scheme 65: Peroxidation of the carbonyl group in unsaturated ketones 228 followed by cyclization of hydroperox...
Scheme 66: CsOH and Et2NH-catalyzed cyclization.
Scheme 67: Preparation of peroxyplakoric acid methyl ethers A and D.
Scheme 68: Hg(OAc)2 in 1,2-dioxane synthesis.
Scheme 69: Reaction of 1,4-diketones 242 with hydrogen peroxide.
Scheme 70: Inramolecular cyclization with oxetane-ring opening.
Scheme 71: Inramolecular cyclization with MsO fragment substitution.
Scheme 72: Synthesis of 1,2-dioxane 255a, a structurally similar compound to natural peroxyplakoric acids.
Scheme 73: Synthesis of 1,2-dioxanes based on the intramolecular cyclization of hydroperoxides containing C=C ...
Scheme 74: Use of BCIH in the intramolecular cyclization.
Scheme 75: Palladium-catalyzed cyclization of δ-unsaturated hydroperoxides 271a–e.
Scheme 76: Intramolecular cyclization of unsaturated peroxyacetals 273a–d.
Scheme 77: Allyltrimethylsilane in the synthesis of 1,2-dioxanes 276a–d.
Scheme 78: Intramolecular cyclization using the electrophilic center of the peroxycarbenium ion 279.
Scheme 79: Synthesis of bicyclic 1,2-dioxanes.
Scheme 80: Preparation of 1,2-dioxane 286.
Scheme 81: Di(tert-butyl)peroxalate-initiated radical cyclization of unsaturated hydroperoxide 287.
Scheme 82: Oxidation of 1,4-betaines 291a–d.
Scheme 83: Synthesis of aminoquinoline-containing 1,2-dioxane 294.
Scheme 84: Synthesis of the sulfonyl-containing 1,2-dioxane.
Scheme 85: Synthesis of the amido-containing 1,2-dioxane 301.
Scheme 86: Reaction of singlet oxygen with the 1,3-diene system 302.
Scheme 87: Synthesis of (+)-premnalane А and 8-epi-premnalane A.
Scheme 88: Synthesis of the diazo group containing 1,2-dioxenes 309a–e.
Figure 4: Plakortolide Е.
Scheme 89: Synthesis of 6-epiplakortolide Е.
Scheme 90: Application of Bu3SnH for the preparation of tetrahydrofuran-containing bicyclic peroxides 318a,b.
Scheme 91: Application of Bu3SnH for the preparation of lactone-containing bicyclic peroxides 320a–f.
Scheme 92: Dihydroxylation of the double bond in the 1,2-dioxene ring 321 with OsO4.
Scheme 93: Epoxidation of 1,2-dioxenes 324.
Scheme 94: Cyclopropanation of the double bond in endoperoxides 327.
Scheme 95: Preparation of pyridazine-containing bicyclic endoperoxides 334a–c.
Scheme 96: Synthesis of 1,2,4-trioxanes 337 by the hydroperoxidation of unsaturated alcohols 335 with 1O2 and ...
Scheme 97: Synthesis of sulfur-containing 1,2,4-trioxanes 339.
Scheme 98: BF3·Et2O-catalyzed synthesis of the 1,2,4-trioxanes 342a–g.
Scheme 99: Photooxidation of enol ethers or vinyl sulfides 343.
Scheme 100: Synthesis of tricyclic peroxide 346.
Scheme 101: Reaction of endoperoxides 348a,b derived from cyclohexadienes 347a,b with 1,4-cyclohexanedione.
Scheme 102: [4 + 2]-Cycloaddition of singlet oxygen to 2Н-pyrans 350.
Scheme 103: Synthesis of 1,2,4-trioxanes 354 using peroxysilylation stage.
Scheme 104: Epoxide-ring opening in 355 with H2O2 followed by the condensation of hydroxy hydroperoxides 356 wi...
Scheme 105: Peroxidation of unsaturated ketones 358 with the H2O2/CF3COOH/H2SO4 system.
Scheme 106: Synthesis of 1,2,4-trioxanes 362 through Et2NH-catalyzed intramolecular cyclization.
Scheme 107: Reduction of the double bond in tricyclic peroxides 363.
Scheme 108: Horner–Wadsworth–Emmons reaction in the presence of peroxide group.
Scheme 109: Reduction of ester group by LiBH4 in the presence of 1,2,4-trioxane moiety.
Scheme 110: Reductive amination of keto-containing 1,2,4-trioxane 370.
Scheme 111: Reductive amination of keto-containing 1,2,4-trioxane and a Fe-containing moiety.
Scheme 112: Acid-catalyzed reactions of Н2О2 with ketones and aldehydes 374.
Scheme 113: Cyclocondensation of carbonyl compounds 376a–d using Me3SiOOSiMe3/CF3SO3SiMe3.
Scheme 114: Peroxidation of 4-methylcyclohexanone (378).
Scheme 115: Synthesis of symmetrical tetraoxanes 382a,b from aldehydes 381a,b.
Scheme 116: Synthesis of unsymmetrical tetraoxanes using of MeReO3.
Scheme 117: Synthesis of symmetrical tetraoxanes using of MeReO3.
Scheme 118: Synthesis of symmetrical tetraoxanes using of MeReO3.
Scheme 119: MeReO3 in the synthesis of symmetrical tetraoxanes with the use of aldehydes.
Scheme 120: Preparation of unsymmmetrical 1,2,4,5-tetraoxanes with high antimalarial activity.
Scheme 121: Re2O7-Catalyzed synthesis of tetraoxanes 398.
Scheme 122: H2SO4-Catalyzed synthesis of steroidal tetraoxanes 401.
Scheme 123: HBF4-Catalyzed condensation of bishydroperoxide 402 with 1,4-cyclohexanedione.
Scheme 124: BF3·Et2O-Catalyzed reaction of gem-bishydroperoxides 404 with enol ethers 405 and acetals 406.
Scheme 125: HBF4-Catalyzed cyclocondensation of bishydroperoxide 410 with ketones.
Scheme 126: Synthesis of symmetrical and unsymmetrical tetraoxanes 413 from benzaldehydes 412.
Scheme 127: Synthesis of bridged 1,2,4,5-tetraoxanes 415a–l from β-diketones 414a–l and H2O2.
Scheme 128: Dimerization of zwitterions 417.
Scheme 129: Ozonolysis of verbenone 419.
Scheme 130: Ozonolysis of O-methyl oxime 424.
Scheme 131: Peroxidation of 1,1,1-trifluorododecan-2-one 426 with oxone.
Scheme 132: Intramolecular cyclization of dialdehyde 428 with H2O2.
Scheme 133: Tetraoxanes 433–435 as by-products in peroxidation of ketals 430–432.
Scheme 134: Transformation of triperoxide 436 in diperoxide 437.
Scheme 135: Preparation and structural modifications of tetraoxanes.
Scheme 136: Structural modifications of steroidal tetraoxanes.
Scheme 137: Synthesis of 1,2,4,5-tetraoxane 454 containing the fluorescent moiety.
Scheme 138: Synthesis of tetraoxane 458 (RKA182).
Beilstein J. Org. Chem. 2013, 9, 2434–2445, doi:10.3762/bjoc.9.281
Graphical Abstract
Scheme 1: Synthesis of D-tagatose from D-galactose using L-arabinose isomerase.
Scheme 2: Synthesis of D-psicose from D-fructose using D-tagatose 3-epimerase/D-psicose 3-epimerase.
Figure 1: The active site in D-psicose 3-epimerase (DPEase) in the presence of D-fructose, showing the metal ...
Scheme 3: Enzymatic synthesis of D-psicose using aldolase FucA.
Scheme 4: Proposed pathway of the D-sorbose synthesis from galactitol or L-glucitol.
Scheme 5: Simultaneous enzymatic synthesis of D-sorbose and D-psicose.
Scheme 6: Biosynthesis of L-tagatose.
Scheme 7: Preparative-scale synthesis of L-tagatose and L-fructose using aldolase.
Scheme 8: Biosynthesis of L-fructose.
Scheme 9: Preparative-scale synthesis of L-fructose using aldolase RhaD.
Scheme 10: Chemoenzymatically synthesis of 1-deoxy-L-fructose [8].
Scheme 11: Potential enzymes (isomerases) for the bioconversion of D-psicose to D-allose.
Scheme 12: Three-step bioconversion of D-glucose to D-allose.
Scheme 13: Biosynthesis of L-glucose.
Scheme 14: Enzymatic synthesis of L-talose and D-gulose.
Scheme 15: Enzymatic synthesis of L-galactose.
Scheme 16: Enzymatic synthesis of L-fucose.
Scheme 17: Synthesis of allitol from D-fructose using a multi-enzyme system.
Scheme 18: Biosynthesis of D-talitol via C-2 reduction of rare sugars.
Scheme 19: Biosynthesis of L-sorbitol via C-2 reduction of rare sugars.
Beilstein J. Org. Chem. 2013, 9, 2048–2078, doi:10.3762/bjoc.9.243
Graphical Abstract
Figure 1: a) Structural features and b) selected examples of non-natural congeners.
Scheme 1: Synthesis of isoindole 18.
Scheme 2: Staining amines with 1,4-diketone 19 (R = H).
Figure 2: Representative members of the indolocarbazole alkaloid family.
Figure 3: Staurosporine (26) bound to the adenosine-binding pocket [19] (from pdb1stc).
Figure 4: Structure of imatinib (34) and midostaurin (35).
Scheme 3: Biosynthesis of staurosporine (26).
Scheme 4: Wood’s synthesis of K-252a via the common intermediate 48.
Scheme 5: Synthesis of 26, 27, 49 and 50 diverging from the common intermediate 48.
Figure 5: Selected members of the cytochalasan alkaloid family.
Scheme 6: Biosynthesis of chaetoglobosin A (57) [56].
Scheme 7: Synthesis of cytochalasin D (70) by Thomas [63].
Scheme 8: Synthesis of L-696,474 (78).
Scheme 9: Synthesis of aldehyde 85 (R = TBDPS).
Scheme 10: Synthesis of (+)-aspergillin PZ (79) by Tanis.
Figure 6: Representative Berberis alkaloids.
Scheme 11: Proposed biosynthetic pathway to chilenine (93).
Scheme 12: Synthesis of magallanesine (97) by Danishefsky [84].
Scheme 13: Kurihara’s synthesis of magallanesine (85).
Scheme 14: Proposed biosynthesis of 113, 117 and 125.
Scheme 15: DNA lesion caused by aristolochic acid I (117) [102].
Scheme 16: Snieckus’ synthesis of piperolactam C (131).
Scheme 17: Synthesis of aristolactam BII (104).
Figure 7: Representative cularine alkaloids.
Scheme 18: Proposed biosynthesis of 136.
Scheme 19: The syntheses of 136 and 137 reported by Castedo and Suau.
Scheme 20: Synthesis of 136 by Couture.
Figure 8: Representative isoindolinone meroterpenoids.
Scheme 21: Postulated biosynthetic pathway for the formation of 156 (adopted from George) [143].
Scheme 22: Synthesis of stachyflin (156) by Katoh [144].
Figure 9: Selected examples of spirodihydrobenzofuranlactams.
Scheme 23: Synthesis of stachybotrylactam I (157).
Scheme 24: Synthesis of pestalachloride A (193) by Schmalz.
Scheme 25: Proposed mechanism for the BF3-catalyzed metal-free carbonyl–olefin metathesis [149].
Scheme 26: Preparation of the isoindoline core of muironolide A (204).
Scheme 27: Proposed biosynthesis of 208.
Scheme 28: Model for the biosynthesis of 215 and 217.
Scheme 29: Synthesis of lactonamycin (215) and lactonamycin Z (217).
Figure 10: Hetisine alkaloids 225–228.
Scheme 30: Biosynthetic proposal for the formation of the hetisine core [167].
Scheme 31: Synthesis of nominine (225).
Beilstein J. Org. Chem. 2013, 9, 1837–1842, doi:10.3762/bjoc.9.214
Graphical Abstract
Figure 1: Overview of some capabilities of an immobilized or in an inert stationary phase dissolved catalyst....
Scheme 1: Diels–Alder reaction of benzenediazonium-2-carboxylate with anthracene-9-derivatives toward triptyc...
Figure 2: The experimental setup and a) the injection sequence protocol of the cryogenic ocRGC measurements b...
Figure 3: Experimental ocRGC chromatogram of 9-anthracenemethanol with benzenediazonium-2-carboxylate. Condit...
Beilstein J. Org. Chem. 2013, 9, 1807–1812, doi:10.3762/bjoc.9.210
Graphical Abstract
Figure 1: Structures of iso-fatty acids.
Scheme 1: Synthesis of iso-C12 1, iso-C13 2, and iso-C14 3 fatty acids from methyl undecylenate (9). Reagents...
Scheme 2: Synthesis of iso-C15 4, iso-C16 5, and iso-C17 6 fatty acids from pentadecanolide (15). Reagents an...
Scheme 3: Synthesis of iso-C18 7 and iso-C19 8 fatty acids from hexadecanolide 23. Reagents and conditions: (...
Scheme 4: Synthesis of (A) 2-methyl- and 2-hydroxy-iso-fatty acids 30 and 32, and (B) the ketone 33. Reagents...
Beilstein J. Org. Chem. 2013, 9, 1652–1662, doi:10.3762/bjoc.9.189
Graphical Abstract
Scheme 1: (a) Synthesis of a polycationic cross-linked hydrogel containing disulfide groups. (b) Reductive cl...
Figure 1: Release of enclosed dyes from polycationic networks containing disulfide bonds after treatment with...
Figure 2: (a) Behavior of poly(DEAAm-co-DMAEMA) (left) and cross-linked poly(DEAAm-co-DMAEMA) (right) in dist...
Scheme 2: Synthesis of poly(DEAAm-co-DMAEMA) discs. (a) Cross-linked discs with CL 1. (b) Cross-linked discs ...
Figure 3: Storage modulus G’ as function of applied shear stress τ for samples 4 and 5 containing different a...
Figure 4: Storage modulus G’ of samples 6 immersed in water (full symbols) or DTT solution (empty symbols) co...
Figure 5: Storage modulus G’ of a polymer disc 6c containing 5.0 mol % CL 1 and 5.0 mol % CL 2 after being im...
Figure 6: Swelling degree Q of polymer discs 4–6 as a function of the amount and type of containing cross-lin...
Beilstein J. Org. Chem. 2013, 9, 1526–1532, doi:10.3762/bjoc.9.174
Graphical Abstract
Scheme 1: Transacetalization of acetal 7.
Scheme 2: Thioacetalization of hexanal with Re2O7.
Scheme 3: Proposed mechanistic pathway.
Beilstein J. Org. Chem. 2013, 9, 1269–1277, doi:10.3762/bjoc.9.143
Graphical Abstract
Scheme 1: Representative C–P bond-forming reactions.
Scheme 2: General equation of homolytic substitution.
Scheme 3: Addition of diphenyl(triphenylstannyl)phosphine.
Scheme 4: Addition of diphenyl(trimethylstannyl)phosphine.
Scheme 5: Plausible mechanism of addition of R3Sn–PPh2.
Scheme 6: Addition of tetraorganodiphosphines to phenylacetylene.
Scheme 7: Plausible mechanism of anti-diphosphination.
Scheme 8: Radical diphosphination for synthesizing fluorescent material.
Scheme 9: Mechanism of thiophosphination with diphenyl(organosulfanyl)phosphine.
Scheme 10: Thiophosphination with S-thiophosphinyl O-ethyl dithiocarbonate.
Scheme 11: Photoinduced selenophosphination of allenes.
Scheme 12: Photoinduced tellurophosphination.
Scheme 13: Decarboxylative phosphorylation of carboxylic acid derivatives.
Scheme 14: Plausible mechanism of decarboxylative phosphorylation.
Scheme 15: Radical phosphination of PTOC esters with white phosphorus.
Scheme 16: Plausible mechanism of radical phosphination (Si = (Me3Si)3Si).
Scheme 17: Stereoselective phosphination leading to (S,S)-aminophosphine derivative.
Figure 1: Calculated reaction profile of homolytic substitution between Ph• and Me3Sn–PPh2 at the B2-PLYP-D/T...
Scheme 18: Phosphination with retention of axial chirality.
Scheme 19: Chemodivergent phosphination.
Scheme 20: Bis(phosphoryl)-bridged biphenyls by radical phosphination.
Scheme 21: Bis(phosphoryl)-bridged ladder triphenylene by radical phosphination.
Scheme 22: Photoinduced phosphination of perfluoroalkyl iodides with tetraphenyldiphosphine.
Scheme 23: Ti(III)-mediated radical phosphination of organic bromides with white phosphorus.