Search for "nomenclature" in Full Text gives 67 result(s) in Beilstein Journal of Organic Chemistry.
Beilstein J. Org. Chem. 2014, 10, 3136–3151, doi:10.3762/bjoc.10.331
Graphical Abstract
Figure 1: Chemical structure of trans-resveratrol (1).
Figure 2: DSC traces of RSV (a), TMA (b), TMA–RSV physical mixture (PM) (c), TMA–RSV preparation by kneading ...
Figure 3: TG (red) and DSC (blue) traces for the hydrated TMA·RSV complex (top), and hot stage micrographs sh...
Figure 4: The two symmetry-independent complex units of TMA·RSV·6.25H2O (A and B), with only the major compon...
Figure 5: Representative atomic labelling for the ordered RSV molecule A (blue) present in host A and the two...
Figure 6: Space-filling representations of the two independent complex units A (a) and B (b) of the complex T...
Figure 7: Crystal packing for the complex TMA·RSV·6.25H2O projected down [010].
Figure 8: The components of the disorder model for RSV in its inclusion complex with TMB (s.o.f. = 0.73 for t...
Figure 9: The asymmetric unit in the crystal of TMB·RSV·5.6H2O (a), and the non-H atom and methylglucose ring...
Figure 10: Space-filling model of the inclusion complex TMB·RSV·5.6H2O showing the inclusion of the RSV molecu...
Figure 11: Packing arrangement in the crystal of TMB·RSV·5.6H2O viewed down [010] (a) and [100] (b). Hydrogen ...
Figure 12: Structure of the host–guest complex DMB·RSV·4.0H2O (a), ring and atomic nomenclature for the host m...
Figure 13: Space-filling model of the inclusion complex DMB·RSV·4.0H2O showing the encapsulation of part of th...
Figure 14: Stereoview of two DMB·RSV·4.0H2O complex units related by a unit translation along the crystal a-ax...
Figure 15: Projections of the crystal structure of the complex DMB·RSV·4H2O along [100] (a) and [010] (b). Hyd...
Figure 16: Solubility of RSV as a function of [β-CD] (blue) and [γ-CD] (red) at 25 °C.
Figure 17: Solubility of RSV as a function of the concentrations of TMB (light blue), DMB (red), HP-β-CD (gree...
Beilstein J. Org. Chem. 2014, 10, 1942–1950, doi:10.3762/bjoc.10.202
Graphical Abstract
Scheme 1: Grignard reaction of aldehyde 3 and oxidation of the resulting mixture of alcohols 4–7. Reagents an...
Figure 1: Molecular structure (DIAMOND drawing with adjacent ChemDraw image) of o-tolyl derivative 8. Atomic ...
Figure 2: Molecular structure (DIAMOND drawing with adjacent ChemDraw image) of benzyl derivative 9. Atomic d...
Scheme 2: Proposed mechanism for Grignard reaction leading to benzyl→o-tolyl rearrangement (path 1). R = sacc...
Scheme 3: Proposed mechanism [24,25] for Grignard reaction leading to 1-naphthylmagnesiumchloride→1-methylnaphthalen...
Beilstein J. Org. Chem. 2014, 10, 794–807, doi:10.3762/bjoc.10.75
Graphical Abstract
Figure 1: Structure of the central cores and lengthening arms.
Scheme 1: Synthesis of compounds of series I–III.
Scheme 2: Synthesis of compounds of series IV–VI.
Figure 2: Chemical formulae of studied compounds I–VI.
Figure 3: DSC plots for compounds a) IIb, b) IVb and c) Vb taken on second heating (upper curve) and cooling ...
Figure 4: Planar texture of Ib in the SmCAPA phase at temperature T = 130 °C (a) without field, and (b) in th...
Figure 5: Planar texture of IIb (a) at the phase transition from the SmAP (upper right corner) to the SmCAPA ...
Figure 6: Switching current for compound IIb at T = 150 °C, taken in the SmCAPA phase at a triangular field, E...
Figure 7: Planar texture of IIb compound the SmCSPA phase at T = 130 °C, (a) without applied field and (b) in...
Figure 8: Temperature dependence of the layer spacing value, d, and intensity of the corresponding X-ray sign...
Figure 9: X-ray patterns of a partially aligned sample of IIb in (a) the SmCG phase at 148 °C and (b) in the ...
Figure 10: 3-Dimensional plot of the imaginary part of permittivity, ε’’, versus temperature and frequency for ...
Figure 11: Temperature dependence of the dielectric strength, Δε, and relaxation frequency, fr, for IIb.
Figure 12: Schematic organization of bent-shaped molecules in layers for the SmCAPA–SmCG–SmCSPA sequence of me...
Beilstein J. Org. Chem. 2013, 9, 1643–1651, doi:10.3762/bjoc.9.188
Graphical Abstract
Figure 1: Structure of the known compound theonellapeptolide Id (1).
Figure 2: Structures of sulfinyltheonellapeptolide (2) and theonellapeptolide If (3).
Figure 3: COSY and key HMBC correlations (left) and MS/MS fragmentations of 2 and its ring-opened methanolysi...
Figure 4: Antiproliferative activity of theonellapeptolides 1–3 on hepatic carcinoma cell line. The MTT assay...
Beilstein J. Org. Chem. 2013, 9, 1285–1295, doi:10.3762/bjoc.9.145
Graphical Abstract
Scheme 1: Proposed mechanisms for the formation of fullerenol anions and distonic radical anions observed by ...
Figure 1: Negative-ion mass spectra for a 0.5 × 10−5 M solution of C60(OH)24 in ultrapure water: (a) full sca...
Scheme 2: Examples of proposed structures for the main deprotonated molecules and final distonic molecular io...
Scheme 3: Proposed (−)ESI-MS ionization mechanisms for fullerenol C60(OH)24 in pure water.
Figure 2: Negative-ion mass spectra of a 0.5 × 10−5 M aqueous solution of C60(OH)24 in ammonia solution: (a) ...
Figure 3: Positive ionization ESI mass spectrum of C60(OH)24 in (a) 3 × 10−1 M (b) 2 × 10−2 M aqueous ammonia...
Scheme 4: Proposed (+)ESI-MS ionization mechanisms for fullerenol C60(OH)24 in ammonia solution.
Beilstein J. Org. Chem. 2013, 9, 681–688, doi:10.3762/bjoc.9.77
Graphical Abstract
Figure 1: Structure of the tropyl radical 1, its cation 2 and the precursor bitropyl 3.
Figure 2: Mass spectra of bitropyl without pyrolysis at 7.8 and 8.7 eV (top and centre trace) and with pyroly...
Figure 3: Threshold photoelectron spectrum of tropyl (black line). The Franck–Condon simulation (red line) is...
Figure 4: TPE spectrum of tropyl (solid line) and cyclopentadienyl (m/z = 65, dashed line) in the 7–13 eV pho...
Figure 5: The shape of the C5H5+ peak in the mass spectrum changes with photon energy. While the peak is symm...
Beilstein J. Org. Chem. 2013, 9, 1–7, doi:10.3762/bjoc.9.1
Graphical Abstract
Figure 1: Configurations and conformations of 5,6-dihydrodibenzo[c,g][1,2]diazocine (1), and DFT (B3LYP/6-31G...
Scheme 1: Synthesis of 3,3’-diamino-EBAB 4 and its acetamide derivative 5.
Figure 2: Crystal structures of the cis isomers of 3,3’-diamino-EBAB 4 and its acetamide derivative 5. The at...
Figure 3: UV–vis spectra of the diazocine derivatives 3,3’-diamino-EBAB 4 and its bisamide derivative 5 in ac...
Figure 4: Absorbances of solutions of 4 and 5 in acetonitrile at 405 nm (red) and 485 nm (blue) in the corres...
Figure 5: DFT-calculated structure (B3LYP/6-31+G**) of a complex of 5 with ethylenediamine as a conceivable m...
Beilstein J. Org. Chem. 2012, 8, 2149–2155, doi:10.3762/bjoc.8.242
Graphical Abstract
Scheme 1: Synthesis of glycoamino acid derivative 3 and its dimer, from the known mannopyranoside 1.
Scheme 2: To obtain the glycocystine derivative 3-dimer from the protected cysteine mannopyranoside precursor ...
Figure 1: In the 1H/13C HMBC NMR spectrum of the S-Fm-protected glycoamino acid derivative 8, protecting-grou...
Scheme 3: Proposed mechanism for the formation of S-Fm-protected 8 from N-Fmoc-protected 7 according to Rich ...
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, 1246–1255, doi:10.3762/bjoc.8.140
Graphical Abstract
Figure 1: Terpenoids 1–5 present in Alloxysta victrix and cis-fused bicyclic iridoids known from other insect...
Figure 2: 70 eV EI-mass spectrum of the iridoid X, a component of the volatile secretions of the parasitoid w...
Figure 3: Structures and gas chromatographic retention times of trans-fused dihydronepetalactones on a conven...
Scheme 1: Route from (S)-pulegone to the mixture of dihydronepetalactones a and b, consequently following Wol...
Figure 4: Configuration of the dihydronepetalactone a.
Figure 5: Route to stereochemically pure trans-fused dihydronepetalactones a–d from (R)-limonene.
Scheme 2: Synthesis of the key compound 16. Reaction conditions: a) O3, MeOH, −50 °C (86%); b) AcOH, piperidi...
Scheme 3: Synthesis of trans,trans-substituted dihydronepetalactone b. Reaction conditions: a) TBDMSCl, imida...
Figure 6: Configurations of compound 24 and the dihydronepetalactone b.
Scheme 4: Synthesis of cis,trans-substituted dihydronepetalactone c. Reaction conditions: a) Crabtree's catal...
Figure 7: Configurations of compound 26 and the dihydronepetalactone c.
Scheme 5: Synthesis of a 2:3 mixture of dihydronepetalactones c and d. Reaction conditions: a) (COCl)2, DMSO,...
Scheme 6: Formal synthesis of a mixture of dihydronepetalactones a and b from (R)-limonene.
Beilstein J. Org. Chem. 2012, 8, 705–711, doi:10.3762/bjoc.8.79
Graphical Abstract
Figure 1: Structure of glycyrrhizin (GL), carbenoxolone (CBX), and spacer analogues.
Scheme 1: Synthesis of methyl 2-haloethyl 1-thio-glucuronide derivatives: (a) 1 M NaOMe, MeOH, −60 °C to −45 ...
Scheme 2: Synthesis of thioalkylglucuronide GA derivatives: (a) DMF, DIPEA, 45–50 °C, 16 h, 79%; (b) TEA, Ac2...
Figure 2: 400 MHz 1H NMR expansion plots of the carbohydrate region of compound 11, recorded at various tempe...
Scheme 3: Synthesis of 3-thioether-bridged glucuronide derivatives: (a) K2CO3, acetone, 60%; (b) 0.8 M NaOMe,...
Beilstein J. Org. Chem. 2012, 8, 349–370, doi:10.3762/bjoc.8.39
Graphical Abstract
Figure 1: Three of the common molecular and supramolecular structural motifs in liquid crystal chemistry: rod...
Figure 2: Schematic representation of the solvent-mediated ligand exchange process, illustrated for the parti...
Figure 3: Chemical structures and LC properties of the rodlike ligands discussed in the text.
Figure 4: Schematic representation of pseudospherical Au NPs coated exclusively with mesogenic rodlike ligand...
Figure 5: TEM images of Au@612 (a) before and (b) after thermal treatment. Below: Proposed model of the nanop...
Figure 6: Ligand deformation at the surface of the gold NPs giving rigid "poles" and a soft equator. Such def...
Figure 7: A simplified illustration of the local rectangular arrangement of nanoparticles in a condensed mixe...
Figure 8: Chemical structures and LC properties of the rodlike ligands discussed in the text.
Figure 9: Schematic drawing of the arrangement of nanoparticles in the columnar phase, as viewed from above (...
Figure 10: The proposed structural models resulting from ligand migration at the NP surface: (a) Smectic (Au@C6...
Figure 11: Reversible migration of the surface ligands as a function of temperature (and phase). Only the blue...
Figure 12: Photochromic and photo-mesogenic rodlike ligands.
Figure 13: Chemical structures and LC properties of side-on mesogens used to coat NPs.
Figure 14: Left: POM image of ligand 12. Right: POM image of Schlieren texture of the hybrid Au@12. Reprinted ...
Figure 15: Threaded nematic texture of Au@ C12/13 as observed by POM at RT. Scale bar = 10 μm. Reprinted with ...
Figure 16: Schematic representation of the gold NP columnar structures. (a) Rhombohedral phase in Au@C12/13 an...
Figure 17:
TEM images of thin films of the phase of Au@C12/13 recorded with the beam (a) parallel to the
pla...
Figure 18: Chemical structures and mesogenic properties of bent-core proto-mesogenic ligands used to coat NPs.
Figure 19: Chemical structures and mesogenic properties of dendritic and proto-dendritic ligands used to coat ...
Figure 20: TEM image showing the arrangement of the hybrid NPs Au@16 into regularly spaced rows. Reprinted wit...
Figure 21: Chemical structures and mesogenic properties of dendritic and proto-dendritic ligands used to coat ...
Figure 22:
Top left: Body-centred (I) cubic lattice of symmetry composed of truncated octahedrons. Top right:...
Figure 23: Model proposed for the organisation of the hybrids within the quasi-nematic mesophase. Reprinted wi...
Figure 24: Mesogenic dendrons used to coat Au NPs.
Figure 25: Chemical structures of the discotic mesogenic ligands used to coat NPs.
Figure 26: TEM images of Au@235,12 prepared from aged solutions stood for 10 days in solutions of (a) 1:1 MeOH...
Figure 27: Some of the various hybrid geometries and packing motifs possible upon ligand grafting to the surfa...
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, 222–233, doi:10.3762/bjoc.7.30
Graphical Abstract
Figure 1: Molecular analogues of the Platonic solids.
Figure 2: The structure of [Mo6Cl8]4+ demonstrates the reciprocal relationship between the cube and the octah...
Figure 3: The deltahedra corresponding to the structures of the closo-boranes [BxHx]2−.
Scheme 1: The first synthesis of a tetrahedrane 19 by Maier.
Scheme 2: The conversion of Dewar benzenes to [3]-prismanes.
Scheme 3: Synthesis of [3]prismane 9 by Katz.
Scheme 4: Synthesis of cubane 10 by Eaton.
Scheme 5: Synthesis of cubane 10 by Pettit.
Scheme 6: Failed routes to [5]-prismane 11.
Scheme 7: Synthesis of [5]prismane 11 by Eaton.
Scheme 8: Retrosynthetic analysis for several approaches to dodecahedrane 16.
Scheme 9: Paquette´s synthesis of dodecahedrane 16.
Scheme 10: Prinzbach´s synthesis of dodecahedrane 16.
Figure 4: The as yet unknown polyhedranes 12–15.
Figure 5: Coupling of two Dewar benzenes.
Scheme 11: A possible route to octahedrane 12.
Scheme 12: A possible route to nonahedrane 13.
Figure 6: Capping [4]peristylane with a four-membered ring system.
Scheme 13: A possible route to decahedrane 14.
Figure 7: A possible route to undecahedrane 15 (left: side view; right: top view).
Scheme 14: Synthetic routes to trigonal prismatic hexasilanes 71a and hexagermanes 71b.
Scheme 15: Synthetic routes to octasila- and octagerma-cubanes.
Scheme 16: Synthesis of an octastannacubane and a decastannapentaprismane.
Scheme 17: Synthesis of a heterocubane.
Figure 8: D3d symmetric C8H8, a bis-truncated cubane.
Beilstein J. Org. Chem. 2010, 6, 810–822, doi:10.3762/bjoc.6.91
Graphical Abstract
Figure 1: The photoaffinity technique allows the identification of ligand binding sites of a receptor protein...
Figure 2: a) Three known photolabile α-D-mannosides that differ in the nature of the photoactive functional g...
Scheme 1: Synthesis of photoactive glycoamino acids 11 and 12. i) Fmoc-Asp-OtBu (for 7), Fmoc-Asp(OtBu)-OH (f...
Scheme 2: Photo-crosslinking experiments with the model peptide angiotensin II and the photoactive mannosides ...
Figure 3: Affino dot–blot with FimHtr and photoactive mannosides applied to nitrocellulose disks. It was irra...
Figure 4: MS/MS spectra of angiotensin II (a) and of angiotensin II, photo-crosslinked with diazirine 2 (b), ...
Beilstein J. Org. Chem. 2009, 5, No. 50, doi:10.3762/bjoc.5.50
Graphical Abstract
Figure 1: Schematic structure of a right-handed chiral nematic (cholesteric) phase. Black arrows represent th...
Figure 2: Structures of the dopants investigated.
Figure 3: Geometry of dopants 1–8. Structures were obtained from DFT calculations at the B3LYP/6-31g** level [58]...
Figure 4: Helicity of the molecular surface of derivative 1 along its principal alignment axes in the liquid ...
Beilstein J. Org. Chem. 2009, 5, No. 33, doi:10.3762/bjoc.5.33
Graphical Abstract
Scheme 1: Aziridine containing natural products.
Scheme 2: Mitomycin structures and nomenclature.
Scheme 3: Base catalysed epimerization of mitomycin B.
Scheme 4: Biosynthesis of mitomycin C (MMC) 7.
Scheme 5: Mode of action of mitomycin C.
Scheme 6: The N–C3–C9a disconnection.
Scheme 7: Danishefsky’s Retrosynthesis of mitomycin K.
Scheme 8: Hetero Diels–Alder reaction en route to mitomycins.
Scheme 9: Nitroso Diels–Alder cycloaddition.
Scheme 10: Frank azide cycloadddition.
Scheme 11: Final steps of mitomycin K synthesis. aPDC, DCM; bPhSCH2N3, PhH, 80 °C; cL-selectride, THF, −78 °C; ...
Scheme 12: Naruta–Maruyama retrosynthesis.
Scheme 13: Synthesis of a leucoaziridinomitosane by nitrene cycloaddition. aAlCl3-Et2O; bNaH, ClCH2OMe; cn-BuL...
Scheme 14: Thermal decomposition of azidoquinone 51.
Scheme 15: Diastereoselectivity during the cycloaddition.
Scheme 16: Oxidation with iodo-azide.
Scheme 17: Williams’ approach towards mitomycins.aDEIPSCl, Imidazole, DCM; bPd/C, HCO2NH4, MeOH; cAllocCl, NaH...
Scheme 18: Synthesis of pyrrolidones by homoconjugate addition.
Scheme 19: Homoconjugate addition on the fully functionalized substrate.
Scheme 20: Introduction of the olefin.
Scheme 21: Retrosynthesis of N–C9a, N–C3 bond formation.
Scheme 22: Synthesis of the pyrrolo[1,2]indole 82 using N-PSP activation.aAc2O, Py; bAc2O, Hg(OAc)2, AcOH, 90%...
Scheme 23: Synthesis of an aziridinomitosane. am-CPBA, DCM then iPr2NH, CCl4 reflux; bK2CO3, MeOH; cBnBr, KH; d...
Scheme 24: Oxidation products of a leucoaziridinomitosane obtained from a Polonovski oxidation.
Scheme 25: Polonovski oxidation of an aziridinomitosane. am-CPBA; bPd/C, H2; cDimethoxypropane, PPTS.
Scheme 26: The C1–C9a disconnection.
Scheme 27: Ziegler synthesis of desmethoxymitomycin A.aIm2C=O, THF; bNH3; cTMSOTf, 2,6-di-tert-butylpyridine, ...
Scheme 28: Transformation of sodium erythorbate.aTBDMSCl; bNaN3; cPPh3; d(Boc)2O, DMAP; eTBAF; fTf2O, Pyr.
Scheme 29: Formation of C9,C10-unsaturation in the mitomycins. am-CPBA, DCM; bO3, MeOH; cMe2S; dKHMDS, (EtO)3P...
Scheme 30: Fragmentation mechanism.
Scheme 31: Michael addition-cyclisation.
Scheme 32: SmI2 8-endo-dig cyclisation.
Scheme 33: Synthesis of pyrrolo[1,2-a]indole by 5-exo-dig radical cyclization.
Scheme 34: The C9–C9a disconnection.
Scheme 35: Intramolecular nitrile oxide cycloaddition.
Scheme 36: Regioselectivity of the INOC.
Scheme 37: Fukuyama’s INOC strategy.
Scheme 38: Synthesis of a mitosane core by rearrangement of a 1-(1-pyrrolidinyl)-1,3-butadiene.
Scheme 39: Sulikowski synthesis of an aziridinomitosene. aPd(Tol3P)2Cl2, Bu3SnF, 140; bH2, Pd/C; cTFAA, Et3N; d...
Scheme 40: Enantioselective carbene insertion.
Scheme 41: Parson’s radical cyclization.
Scheme 42: Cha’s mitomycin B core synthesis.
Scheme 43: The N-aromatic disconnection.
Scheme 44: Kishi retrosynthesis.
Scheme 45: Kishi synthesis of a starting material. aallyl bromide, K2CO3, acetone, reflux; bN,N-Dimethylanilin...
Scheme 46: Kishi synthesis of MMC 7. aLDA, THF, −78 °C then PhSeBr, THF, −78 °C; bH2O2, THF-EtOAc; cDIBAL, DCM...
Scheme 47: Acid catalyzed degradation of MMC 7.
Scheme 48: In vivo formation of apomitomycin B.
Scheme 49: Advanced intermediate for apomitomycin B synthesis.
Scheme 50: Remers synthesis of a functionalized mitosene. aTMSCl, Et3N, ZnCl2 then NBS; bAcOK; cNH2OH; dPd/C, H...
Scheme 51: Coleman synthesis of desmethoxymitomycin A. aSnCl2, PhSH, Et3N, CH3CN; bClCO2Bn, Et3N; cPPh3, DIAD,...
Scheme 52: Transition state and pyrrolidine synthesis.
Scheme 53: Air oxidation of mitosanes and aziridinomitosanes.
Scheme 54: The C9-aromatic disconnection.
Scheme 55: Synthesis of the aziridine precursor. aLHMDS, THF; bNaOH; c(s)-α-Me-BnNH2, DCC, HOBT; dDIBAL; eK2CO3...
Scheme 56: Synthesis of 206 via enamine conjugate addition.
Scheme 57: Rapoport synthesis of an aziridinomitosene.
Scheme 58: One pot synthesis of a mitomycin analog.
Scheme 59: Synthesis of compound 218 via intramolecular Heck coupling. aEtMgCl, THF, then 220; bMsCl, Et3N; cN...
Scheme 60: Elaboration of indole 223. aEt3N, Ac2O; bAcOH; cSOCl2, Et3N; dNaN3, DMF; eH2SO4, THF; fK2CO3, MeOH; ...
Scheme 61: C9-C9a functionalization from indole.
Scheme 62: Synthesis of mitomycin K. a2 equiv. MoO5.HMPA, MeOH; bPPh3, Et3N, THF-H2O; cMeOTf, Py, DCM; dMe3SiCH...
Scheme 63: Configurational stability of mitomycin K derivatives.
Scheme 64: Epimerization of carbon C9a in compound 227b.
Scheme 65: Corey–Chaykovsky synthesis of indol 235.
Scheme 66: Cory intramolecular aza-Darzens reaction for the formation of aziridinomitosene 239.
Scheme 67: Jimenez synthesis of aziridinomitosene 242.
Scheme 68: Von Braun opening of indoline 244.
Scheme 69: C9a oxidation of an aziridinomitosane with DDQ/OsO4.
Scheme 70: Synthesis of epi-mitomycin K. aNaH, Me2SO4; bH2, Pd/C; cMitscher reagent [165]; d[(trimethylsilyl)methyl...
Scheme 71: Mitomycins rearrangement.
Scheme 72: Fukuyama’s retrosynthesis.
Scheme 73: [2+3] Cycloaddition en route to isomitomycin A. aToluene, 110 °C; bDIBAL, THF, −78 °C; cAc2O, Py.; d...
Scheme 74: Final steps of Fukuyama’s synthesis.
Scheme 75: “Crisscross annulation”.
Scheme 76: Synthesis of 274; the 8-membered ring 274 was made using a crisscross annulation. a20% Pd(OH)2/C, H2...
Scheme 77: Conformational analysis of compound 273 and 275.
Scheme 78: Synthesis of a mitomycin analog. aNa2S2O4, H2O, DCM; bBnBr (10 equiv), K2CO3, 18-crown-6 (cat.), TH...
Scheme 79: Vedejs retrosynthesis.
Scheme 80: Formation of the azomethine ylide.
Scheme 81: Vedejs second synthesis of an aziridinomitosene. aDIBAL; bTPAP, NMO; c287; dTBSCl, imidazole.
Scheme 82: Trityl deprotection and new aziridine protecting group 300.
Scheme 83: Ene reaction towards benzazocinones.
Scheme 84: Benzazocenols via homo-Brook rearrangement.
Scheme 85: Pt-catalyzed [3+2] cycloaddition.
Scheme 86: Carbonylative lactamization entry to benzazocenols. aZn(OTf)2, (+)-N-methylephedrine, Et3N, TMS-ace...
Scheme 87: 8 membered ring formation by RCM. aBOC2O, NaHCO3; bTBSCl, Imidazole, DMF; callyl bromide, NaH, DMF; ...
Scheme 88: Aziridinomitosene synthesis. aTMSN3; bTFA; cPOCl3, DMF; dNaClO2, NaH2PO4, 2-methyl-2-butene; eMeI, ...
Scheme 89: Metathesis from an indole.
Scheme 90: Synthesis of early biosynthetic intermediates of mitomycins.