Search for "debromination" in Full Text gives 32 result(s) in Beilstein Journal of Organic Chemistry.
Beilstein J. Org. Chem. 2012, 8, 1936–1998, doi:10.3762/bjoc.8.225
Graphical Abstract
Figure 1: Loschmidt’s structure proposal for benzene (1) (Scheme 181 from [3]) and the corresponding modern stru...
Figure 2: The first isolated bisallenes.
Figure 3: Carbon skeletons of selected bisallenes discussed in this review.
Scheme 1: The preparation of 1,2,4,5-hexatetraene (2).
Scheme 2: The preparation of a conjugated bisallene by the DMS-protocol.
Scheme 3: Preparation of the 3-deuterio- and 3,4-dideuterio derivatives of 24.
Scheme 4: A versatile method to prepare alkylated conjugated bisallenes and other allenes.
Scheme 5: A preparation of 3,4-dimethyl-1,2,4,5-hexatetraene (38).
Scheme 6: A (C6 + 0)-approach to 1,2,4,5-hexatetraene (2).
Scheme 7: The preparation of a fully alkylated bisallenes from a 2,4-hexadiyne-1,6-diol diacetate.
Scheme 8: The preparation of the first phenyl-substituted conjugated bisallenes 3 and 4.
Scheme 9: Selective hydrogenation of [5]cumulenes to conjugated bisallenes: another (C6 + 0)-route.
Scheme 10: Aryl-substituted conjugated bisallenes by a (C3 + C3)-approach.
Scheme 11: Hexaphenyl-1,2,4,5-hexatetraene (59) by a (C3 + C3)-approach.
Scheme 12: An allenation route to conjugated bisallenes.
Scheme 13: The preparation of 3,4-difunctionalized conjugated bisallenes.
Scheme 14: Problems during the preparation of sulfur-substituted conjugated bisallenes.
Scheme 15: The preparation of 3,4-dibromo bisallenes.
Scheme 16: Generation of allenolates by an oxy-Cope rearrangement.
Scheme 17: A linear trimerization of alkynes to conjugated bisallenes: a (C2 + C2 + C2)-protocol.
Scheme 18: Preparation of a TMS-substituted conjugated bisallene by a C3-dimerization route.
Scheme 19: A bis(trimethylsilyl)bisallene by a C3-coupling protocol.
Scheme 20: The rearrangement of highly substituted benzene derivatives into their conjugated bisallenic isomer...
Scheme 21: From fully substituted benzene derivatives to fully substituted bisallenes.
Scheme 22: From a bicyclopropenyl to a conjugated bisallene derivative.
Scheme 23: The conversion of a bismethylenecyclobutene into a conjugated bisallene.
Scheme 24: The preparation of monofunctionalized bisallenes.
Scheme 25: Preparation of bisallene diols and their cyclization to dihydrofurans.
Scheme 26: A 3,4-difunctionalized conjugated bisallene by a C3-coupling process.
Scheme 27: Preparation of a bisallenic diketone by a coupling reaction.
Scheme 28: Sulfur and selenium-substituted bisallenes by a [2.3]sigmatropic rearrangement.
Scheme 29: The biallenylation of azetidinones.
Scheme 30: The preparation of a fully ferrocenylated conjugated bisallene.
Scheme 31: The first isomerization of a 1,5-hexadiyne to a 1,2,4,5-hexatetraene.
Scheme 32: The preparation of alkynyl-substituted bisallenes by a C3-dimerization protocol.
Scheme 33: Preparation of another completely ferrocenylated bisallene.
Scheme 34: The cyclization of 1,5-hexadiyne (129) to 3,4-bismethylenecyclobutene (130) via 1,2,4,5-hexatetraen...
Scheme 35: Stereochemistry of the thermal cyclization of bisallenes to bismethylenecyclobutenes.
Scheme 36: Bisallene→bismethylenecyclobutene ring closures in the solid state.
Scheme 37: A bisallene cyclization/dimerization reaction.
Scheme 38: A selection of Diels–Alder additions of 1,2,4,5-hexatetraene with various double-bond dienophiles.
Scheme 39: The stereochemistry of the [2 + 4] cycloaddition to conjugated bisallenes.
Scheme 40: Preparation of azetidinone derivatives from conjugated bisallenes.
Scheme 41: Cycloaddition of heterodienophiles to a conjugated bisallene.
Scheme 42: Addition of triple-bond dienophiles to conjugated bisallenes.
Scheme 43: Sulfur dioxide addition to conjugated bisallenes.
Scheme 44: The addition of a germylene to a conjugated bisallene.
Scheme 45: Trapping of conjugated bisallenes with phosphinidenes.
Scheme 46: The cyclopropanantion of 1,2,4,5-hexatetraene (2).
Scheme 47: Photochemical reactions involving conjugated bisallenes.
Scheme 48: Base-catalyzed isomerizations of conjugated bisallenes.
Scheme 49: Ionic additions to a conjugated bisallene.
Scheme 50: Oxidation reactions of a conjugated bisallene.
Scheme 51: The mechanism of oxidation of the bisallene 24.
Scheme 52: CuCl-catalyzed cyclization of 1,2,4,5-hexatetraene (2).
Scheme 53: The conversion of conjugated bisallenes into cyclopentenones.
Scheme 54: Oligomerization of a conjugated bisallene by nickel catalysts.
Scheme 55: Generation of 1,2,5,6-heptatetraene (229) as a reaction intermediate.
Scheme 56: The preparation of a stable derivative of 1,2,5,6-heptatetraene.
Scheme 57: A bisallene with a carbonyl group as a spacer element.
Scheme 58: The first preparation of 1,2,6,7-octatetraene (242).
Scheme 59: Preparation of 1,2,6,7-octatetraenes by (C4 + C4)-coupling of enynes.
Scheme 60: Preparation of 1,2,6,7-octatetraenes by (C4 + C4)-coupling of homoallenyl bromides.
Scheme 61: Preparation of 1,2,6,7-octatetraenes by alkylation of propargylic substrates.
Scheme 62: Preparation of two highly functionalized 1,2,6,7-octatetraenes.
Scheme 63: Preparation of several higher α,ω-bisallenes.
Scheme 64: Preparation of different alkyl derivatives of α,ω-bisallenes.
Scheme 65: The preparation of functionalized 1,2,7,8-nonatetraene derivatives.
Scheme 66: Preparation of functionalized α,ω-bisallenes.
Scheme 67: The preparation of an α,ω-bisallene by direct homologation of an α,ω-bisalkyne.
Scheme 68: The gas-phase pyrolysis of 4,4-dimethyl-1,2,5,6-heptatetraene (237).
Scheme 69: Gas-phase pyrolysis of 1,2,6,7-octatetraene (242).
Scheme 70: The cyclopropanation of 1,2,6,7-octatetraene (242).
Scheme 71: Intramolecular cyclization of 1,2,6,7-octatetraene derivatives.
Scheme 72: The gas-phase pyrolysis of 1,2,7,8-nonatetraene (265) and 1,2,8,9-decatetraene (266).
Scheme 73: Rh-catalyzed cyclization of a functionalized 1,2,7,8-nonatetraene.
Scheme 74: A triple cyclization involving two different allenic substrates.
Scheme 75: Bicyclization of keto derivatives of 1,2,7,8-nonatetraene.
Scheme 76: The preparation of complex organic compounds from functionalized bisallenes.
Scheme 77: Cycloisomerization of an α,ω-bisallene containing a C9 tether.
Scheme 78: Organoborane polymers from α,ω-bisallenes.
Scheme 79: Preparation of trans- (337) and cis-1,2,4,6,7-octapentaene (341).
Scheme 80: The preparation of 4-methylene-1,2,5,6-heptatetraene (349).
Scheme 81: The preparation of acetylenic bisallenes.
Scheme 82: The preparation of derivatives of hydrocarbon 351.
Scheme 83: The construction of macrocyclic alleno-acetylenes.
Scheme 84: Preparation and reactions of 4,5-bismethylene-1,2,6,7-octatetraene (365).
Scheme 85: Preparation of 1,2-bis(propadienyl)benzene (370).
Scheme 86: The preparation of 1,4-bis(propadienyl)benzene (376).
Scheme 87: The preparation of aromatic and heteroaromatic bisallenes by metal-mediated coupling reactions.
Scheme 88: Double cyclization of an aromatic bisallene.
Scheme 89: Preparation of an allenic [15]paracyclophane by a ring-closing metathesis reaction of an aromatic α...
Scheme 90: Preparation of a macrocyclic ring system containing 1,4-bis(propadienyl)benzene units.
Scheme 91: Preparation of copolymers from 1,4-bis(propadienyl)benzene (376).
Scheme 92: A boration/copolymerization sequence of an aromatic bisallene and an aromatic bisacetylene.
Scheme 93: Formation of a layered aromatic bisallene.
Figure 4: The first members of the semicyclic bisallene series.
Scheme 94: Preparation of the first bis(vinylidene)cyclobutane derivative.
Scheme 95: Dimerization of strain-activated cumulenes to bis(vinylidene)cyclobutanes.
Scheme 96: Photodimerization of two fully substituted butatrienes in the solid state.
Scheme 97: Preparation of the two parent bis(vinylidene)cyclobutanes.
Scheme 98: The preparation of 1,3-bis(vinylidene)cyclopentane and its thermal isomerization.
Scheme 99: The preparation of the isomeric bis(vinylidene)cyclohexanes.
Scheme 100: Bi- and tricyclic conjugated bisallenes.
Scheme 101: A selection of polycyclic bisallenes.
Scheme 102: The first endocyclic bisallenes.
Figure 5: The stereochemistry of 1,2,6,7-cyclodecatetraene.
Scheme 103: The preparation of several endocyclic bisallenes.
Scheme 104: Synthesis of diastereomeric derivatives of 1,2,6,7-cyclodecatetraene.
Scheme 105: Preparation of a derivative of 1,2,8,9-cyclotetradecatetraene.
Scheme 106: The preparation of keto derivatives of cyclic bisallenes.
Scheme 107: The preparation of cyclic biscumulenic ring systems.
Scheme 108: Cyclic bisallenes in natural- and non-natural-product chemistry.
Scheme 109: The preparation of iron carbonyl complexes from cyclic bisallenes.
Figure 6: A selection of unknown exocyclic bisallenes that should have interesting chemical properties.
Scheme 110: The thermal isomerization of 1,2-diethynylcyclopropanes and -cyclobutanes.
Scheme 111: Intermediate generation of a cyclooctapentaene.
Scheme 112: Attempted preparation of a cyclodecahexaene.
Scheme 113: The thermal isomerization of 1,5,9-cyclododecatriyne (511) into [6]radialene (514).
Scheme 114: An isomerization involving a diketone derived from a conjugated bisallene.
Scheme 115: Typical reaction modes of heteroorganic bisallenes.
Scheme 116: Generation and thermal behavior of acyclic hetero-organic bisallenes.
Scheme 117: Generation of bis(propadienyl)thioether.
Scheme 118: The preparation of a bisallenic sulfone and its thermal isomerization.
Scheme 119: Bromination of the bisallenic sulfone 535.
Scheme 120: Metalation/hydrolysis of the bisallenic sulfone 535.
Scheme 121: Aromatic compounds from hetero bisallenes.
Scheme 122: Isomerization/cyclization of bispropargylic ethers.
Scheme 123: The preparation of novel aromatic systems by base-catalyzed isomerization of bispropargyl ethers.
Scheme 124: The isomerization of bisacetylenic thioethers to bicyclic thiophenes.
Scheme 125: Aromatization of macrocyclic bispropargylic sulfides.
Scheme 126: Preparation of ansa-compounds from macrocyclic bispropargyl thioethers.
Scheme 127: Alternate route for cyclization of a heterorganic bisallene.
Scheme 128: Multiple isomerization/cyclization of “double” bispropargylic thioethers.
Scheme 129: Preparation of a bisallenyl disulfide and its subsequent bicyclization.
Scheme 130: Thermal cyclization of a bisallenyl thiosulfonate.
Scheme 131: Some reactions of heteroorganic bisallenes with two sulfur atoms.
Scheme 132: Further methods for the preparation of heteroorganic bisallenes.
Scheme 133: Cyclization reactions of heteroorganic bisallenes.
Scheme 134: Thermal cycloadditions of bisallenic tertiary amines.
Scheme 135: Cyclization of a bisallenic tertiary amine in the presence of a transition-metal catalyst.
Scheme 136: A Pauson–Khand reaction of a bisallenic ether.
Scheme 137: Formation of a 2:1adduct from two allenic substrates.
Scheme 138: A ring-forming silastannylation of a bisallenic tertiary amine.
Scheme 139: A three-component cyclization involving a heterorganic bisallene.
Scheme 140: Atom-economic construction of a complex organic framework from a heterorganic α,ω-bisallene.
Beilstein J. Org. Chem. 2012, 8, 1400–1405, doi:10.3762/bjoc.8.162
Graphical Abstract
Figure 1: Related compounds of eletriptan hydrobromide.
Scheme 1: Synthetic route of eletriptan hydrobromide. Reagents and conditions: (i) Acetic anhydride, TEA, DMF...
Scheme 2: Dimerization of 13. Reagents and conditions: (i) NaH, THF, 30–35 °C, 2 h; 11.6% yield after column ...
Scheme 3: Formation of the isomers 3 and 4. Reagents and conditions: (i) Aqueous hydrogen peroxide, methanol,...
Scheme 4: Synthesis of impurity 5. Reagents and conditions: (i) Acetic anhydride, TEA, DMF, 90–100 °C; (ii) p...
Scheme 5: Debromination of 9 to 6. Reagents and conditions: Palladium on carbon, ethanol, ca. 7 bar, 25–30 °C...
Scheme 6: Formation of 7. Reagents, conditions: (i) (a) K2CO3, methanol, reflux, 2 days; 40% yield after colu...
Scheme 7: Synthesis of the tetracyclic compound 7. Reagents and conditions: (i) aqueous hydrogen peroxide, wa...
Beilstein J. Org. Chem. 2012, 8, 259–265, doi:10.3762/bjoc.8.27
Graphical Abstract
Scheme 1: Retrosynthetic analysis of the designed target molecules.
Scheme 2: Synthetic routes for 4-chlorophenyl tribromomethyl sulfone (1).
Scheme 3: Halogenation/nitration sequence for 4-halogenphenyl methyl sulfones 4 and 4'.
Scheme 4: SNAr transformations of sulfone 6.
Scheme 5: Preparation of phenylhydrazones 8a–8l.
Scheme 6: Products of the nitro group reduction of sulfone 7a.
Scheme 7: Synthesis of benzimidazole derivatives 11a–11g.
Scheme 8: Preparation and further transformation of 2-mercaptobenzimidazole 11h.
Beilstein J. Org. Chem. 2012, 8, 201–226, doi:10.3762/bjoc.8.22
Graphical Abstract
Figure 1: Calixarenes and expanded calixarenes: p-tert-Butylcalix[4]arene (1), p-tert-butyldihomooxacalix[4]a...
Figure 2: Conventional nomenclature for oxacalix[n]arenes.
Scheme 1: Synthesis of oxacalix[3]arenes: (i) Formaldehyde (37% aq), NaOH (aq), 1,4-dioxane; glacial acetic a...
Figure 3: p-tert-Butyloctahomotetraoxacalix[4]arene (4a) [16].
Figure 4: X-ray crystal structure of 3a showing phenolic hydrogen bonding (IUCr ID AS0508) [17].
Scheme 2: Stepwise synthesis of asymmetric oxacalix[3]arenes: (i) MOMCl, Adogen®464; (ii) 2,2-dimethoxypropan...
Figure 5: X-ray crystal structure of heptahomotetraoxacalix[3]arene 5 (CCDC ID 166088) [21].
Scheme 3: Oxacalix[3]arene synthesis by reductive coupling: (i) Me3SiOTf, Et3SiH, CH2Cl2; R1, R2 = I, Br, ben...
Scheme 4: Oxacalix[3]naphthalene: (i) HClO4 (aq), wet CHCl3 (R = tert-butyl, 6a, H, 6b) [20].
Figure 6: Conformers of 3a.
Scheme 5: Origin of the 25:75 cone:partial-cone statistical distribution of O-substituted oxacalix[3]arenes (p...
Scheme 6: Synthesis of alkyl ethers 7–10: (i) Alkyl halide, NaH, DMF [24].
Scheme 7: Synthesis of a pyridyl derivative 11a: (i) Picolyl chloride hydrochloride, NaH, DMF [26,27].
Figure 7: X-ray crystal structure of partial-cone 11a (CCDC ID 150580) [26].
Scheme 8: Lower-rim ethyl ester synthesis: (i) Ethyl bromoacetate, NaH, t-BuOK or alkali metal carbonate, THF...
Scheme 9: Forming chiral receptor 13: (i) Ethyl bromoacetate, NaH, THF; (ii) NaOH, H2O/1,4-dioxane; (iii) S-P...
Figure 8: X-ray crystal structure of 16 (IUCr ID PA1110) [32].
Scheme 10: Lower rim N,N-diethylamide 17a: (i) N,N-Diethylchloroacetamide, NaH, t-BuOK or alkali metal carbona...
Scheme 11: Capping the lower rim: (i) N,N-Diethylchloroacetamide, NaH, THF; (ii) NaOH, H2O/1,4-dioxane; (iii) ...
Figure 9: X-ray crystal structure of 18 (CCDC ID 142599) [33].
Scheme 12: Extending the lower rim: (i) Glycine methyl ester, HOBt, dicyclohexycarbodiimide (DCC), CH2Cl2; (ii...
Scheme 13: Synthesis of N-hydroxypyrazinone derivative 23: (i) 1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide...
Scheme 14: Synthesis of 24: (i) 1-Adamantyl bromomethyl ketone, NaH, THF [39].
Scheme 15: Synthesis of 25 and 26: (i) (Diphenylphosphino)methyl tosylate, NaH, toluene; (ii) phenylsilane, to...
Figure 10: X-ray crystal structure of 27 in the partial-cone conformer (CCDC ID SUP 90399) [41].
Scheme 16: Synthesis of strapped oxacalix[3]arene derivatives 28 and 29: (i) N,N’-Bis(chloroacetyl)-1,2-ethyle...
Figure 11: A chiral oxacalix[3]arene [45].
Figure 12: X-ray crystal structure of asymmetric oxacalix[3]arene 30 incorporating t-Bu, iPr and Et groups (CC...
Scheme 17: Reactions of an oxacalix[3]arene incorporating an upper-rim Br atom with (i) Pd(OAc)2, PPh3, HCO2H,...
Scheme 18: Synthesis of acid 39: (i) NaOH, EtOH/H2O, HCl (aq) [47].
Figure 13: Two forms of dimeric oxacalix[3]arene 40 [47].
Scheme 19: Capping the upper rim: (i) t-BuLi, THF, −78 °C; (ii) NaBH4, THF/EtOH; (iii) 1,3,5-tris(bromomethyl)...
Figure 14: Oxacalix[3]arene capsules 46 and 47 formed through coordination chemistry [52,53].
Figure 15: X-ray crystal structure of the 3b-vanadyl complex (CCDC ID 240185) [57].
Scheme 20: Effect of Ti(IV)/SiO2 on 3a: (i) Ti(OiPr)4, toluene; (ii) triphenylsilanol, toluene; (iii) partiall...
Figure 16: X-ray crystal structures of oxacalix[3]arene complexes with rhenium: 3b∙Re(CO)3 (CCDC ID 620981, le...
Figure 17: X-ray crystal structure of the La2·3a2 complex (CSD ID TIXXUT) [60].
Figure 18: X-ray crystal structures of [3a∙UO2]− with a cavity-bound cation (CCDC ID 135575, left) and without...
Figure 19: X-ray crystal structure of a supramolecule comprising two [3g·UO2]− complexes that encapsulate a di...
Figure 20: X-ray crystal structure of oxacalix[3]arene 49 capable of chiral selectivity (CSD ID HIGMUF) [65].
Figure 21: The structure of derivative 50 incorporating a Reichardt dye [66].
Figure 22: Phosphorylated oxacalix[3]arene complexes with transition metals: (Left to right) 26∙Au, 26∙Mo(CO)3...
Figure 23: X-ray crystal structure of [17a·HgCl2]2 (CCDC ID 168653) [69].
Figure 24: X-ray crystal structures of 3f with C60 (CCDC ID 182801, left) [76] and a 1,4-bis(9-fluorenyl) C60 deri...
Figure 25: X-Ray crystal structure of 3i and 6a encapsulating C60 (CCDC ID 102473 and 166077) [23,79].
Figure 26: A C60 complexing cationic oxacalix[3]arene 51 [81].
Figure 27: An oxacalix[3]arene-C60 self-associating system 53 [87].
Scheme 21: Synthesis of fluorescent pyrene derivative 55: (i) Propargyl bromide, acetone; (ii) CuI, 1-azidomet...
Scheme 22: Synthesis of responsive rhodamine derivative 57: (i) DCC, CH2Cl2 [91].
Scheme 23: Synthesis of nitrobenzyl derivative 58: (i) 1-Bromo-4-nitrobenzyl acetate, K2CO3, refluxing acetone...
Figure 28: X-ray crystal structure of [Na2∙17a](PF6)2 (CCDC ID 116656) [97].
Beilstein J. Org. Chem. 2011, 7, 525–542, doi:10.3762/bjoc.7.61
Graphical Abstract
Scheme 1: Photochemistry of benzene.
Scheme 2: Three distinct modes of photocycloaddition of arenes to alkenes.
Scheme 3: Mode selectivity with respect of the free enthalpy of the radical ion pair formation.
Scheme 4: Photocycloaddition shows lack of mode selectivity.
Scheme 5: Mechanism of the meta photocycloaddition.
Scheme 6: Evidence of biradiacal involved in meta photocycloaddition by Reedich and Sheridan.
Scheme 7: Regioselectivity with electron withdrawing and electron donating substituents.
Scheme 8: Closure of cyclopropyl ring affords regioisomers.
Scheme 9: Endo versus exo product in the photocycloaddition of pentene to anisole [33].
Scheme 10: Regio- and stereoselectivity in the photocycloaddition of cyclopentene with a protected isoindoline....
Scheme 11: 2,6- and 1,3-addition in intramolecular approach.
Scheme 12: Linear and angularly fused isomers can be obtained upon intramolecular 1,3-addition.
Scheme 13: Synthesis of α-cedrene via diastereoselective meta photocycloaddition.
Scheme 14: Asymmetric meta photocycloaddition introduced by chirality of tether at position 2.
Scheme 15: Enantioselective meta photocycloaddition in β-cyclodextrin cavity.
Scheme 16: Vinylcyclopropane–cyclopentene rearrangement.
Scheme 17: Further diversification possibilities of the meta photocycloaddition product.
Scheme 18: Double [3 + 2] photocycloaddition reaction affording fenestrane.
Scheme 19: Total synthesis of Penifulvin B.
Scheme 20: Towards the total synthesis of Lacifodilactone F.
Scheme 21: Regioselectivity of ortho photocycloaddition in polarized intermediates.
Scheme 22: Exo and endo selectivity in ortho photocycloaddition.
Scheme 23: Ortho photocycloaddition of alkanophenones.
Scheme 24: Photocycloadditions to naphtalenes usually in an [2 + 2] mode [79].
Scheme 25: Ortho photocycloaddition followed by rearrangements.
Scheme 26: Stable [2 + 2] photocycloadducts.
Scheme 27: Ortho photocycloadditions with alkynes.
Scheme 28: Intramolecular ortho photocycloaddition and rearrangement thereof.
Scheme 29: Intramolecular ortho photocycloaddition to access propellanes.
Scheme 30: Para photocycloaddition with allene.
Scheme 31: Photocycloadditions of dianthryls.
Scheme 32: Photocycloaddition of enone with benzene.
Scheme 33: Intramolecular photocycloaddition affording multicyclic compounds via [4 + 2].
Scheme 34: Photocycloaddition described by Sakamoto et al.
Scheme 35: Proposed mechanism by Sakamoto et al.
Scheme 36: Photocycloaddition described by Jones et al.
Scheme 37: Proposed mechanism for the formation of benzoxepine by Jones et al.
Scheme 38: Photocycloaddition observed by Griesbeck et al.
Scheme 39: Mechanism proposed by Griesbeck et al.
Scheme 40: Intramolecular photocycloaddition of allenes to benzaldehydes.
Beilstein J. Org. Chem. 2010, 6, No. 30, doi:10.3762/bjoc.6.30
Graphical Abstract
Scheme 1: Synthesis of 1 and 3. (a) Pyridazine, toluene, reflux, 20 h; (b) NaI, DMF, 65 °C, 15 h.
Scheme 2: Synthesis of 2 and 4. (a) NaI, DMF, 65 °C, 24 h; (b) AgSbF6, THF.
Figure 1: ORTEP drawing of the crystal structures: a) 2 and b) 3. For additional perspective representations ...
Figure 2: a) ORTEP drawing of the crystal structure of 4. Ag+ and Ag+, describe the two disordered positions ...
Scheme 3: Synthesis of 5 and 6. (a) Toluene, 90 °C, 15 h.
Figure 3: ORTEP drawing of the crystal structures: a) 5b and b) 6. For additional perspective representations...
Beilstein J. Org. Chem. 2007, 3, No. 23, doi:10.1186/1860-5397-3-23
Graphical Abstract
Figure 1: Thiophene structures 1, 2, and 3.
Figure 2: XR-693 and XR-906.
Scheme 1: Synthesis and Reactivity of 2,4,5-Tribromo-3-methylthiophene. Initial Bromination Approaches.
Scheme 2: Routes to 4-Bromo-3-methyl-2-thiopheneacid Chloride, 1, From 3-Methylthiophene, 4. (a) NBS/AcOH, 64...
Scheme 3: Vapor Phase Chlorination of 2-Thiophenecarbonitrile.
Scheme 4: Synthesis of 3,4,5-Trichloro-2-thiopheneacid Chloride, 2. (a) 1. n-BuLi/MTBE, -60°C, 2. CO2; or 1. ...
Scheme 5: Metal-Halogen Exchange in THF Solvent.