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Redaktion: Ernst Schaumann
Sulfur-Mediated Rearrangement I
erschienen Februar 2007 188 Seiten, Gebunden
Springer-Verlag GmbH & Co. KG | ISBN: 3540680977
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| VORWORT | öffnen |
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PrefaceIn their analysis of experiments and in their planning of syntheses, organic chemists consciously or unconsciously tend to use the principle of least motion, the chemical equivalent of Occam's razor. In rearrangement reactions this principle is violated and may make rearrangements problematic reactions. At the same time, there is always fascination in the unexpected and so rearrangement reactions are also an attractive field of study. Consequently, our understanding of rearrangement react...
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TOPICS IN CURRENT CHEMISTRY Sulfur-Mediated Rearrangements I Volume Editor E. Schaumann E. Schaumann Sulfur is More Than the Fat Brother of Oxygen. An Overview of Organosulfur Chemistry S. Akai • Y. Kita Recent Advances in Pummerer Reactions A.W. Sromek 1,2-Sulfur Migrations V. Gevorgyan S.K. Bur 1,3-Sulfur Shifts: Mechanism and Synthetic Utility ISBN 978-3-540-68097-0 springer.com [weiter lesen] |
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| INHALTSVERZEICHNIS | öffnen |
Contents Sulfur is More Than the Fat Brother of Oxygen. An Overview of Organosulfur Chemistry E. Schaumann 1 Recent Advances in Pummerer Reactions S. Akai Y. Kita 35 1,2-Sulfur Migrations A. W. Sromek V. Gevorgyan 77 1,3-Sulfur Shifts: Mechanism and Synthetic Utility S.K. Bur 125 Author Index Volumes 251-274173 Subject Index 183
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Subject Index AAcetogenin 38 Acetyl coenzyme A 3 Acetylation 36 Acyl coenzyme A 3 Acylcyclopropanes 5 - S-Adenosylmethionine 3 Allyl alcohols 25 Allyl sulfides 126 Allyl sulfones 148 Allyl sulfoxides 25, 143 Allyl thioethers 79 Allyl thiols 81 Allylic reversal 127 - 1, 4-Aminoalcohols 16 - ß -Aminoenones 23 - ß -Aminosulfoxides 65 Aniline 57 Arylsulfanylindolenine, sulfenamide 128 Asymmetric reaction 35 - N-Benzensulfinyl-tosylamide 15 B N-Benzensulfinyl-tosylamide 15 Benzimidazoles 128 Benzofuran neolignans 57 Benzothiazines 132 Biomolecules, sulfur-containing 4 - Biotin 3 Bis(o-aminophenyl)disulfides 132 Bond-forming reactions, carbon-carbon 35 - interintramolecular 41, 42 - Pummerer reaction-initiated 41 CCamphorsulfonic acid 18 Carbanion stabilization 12 Carbene, 1, 2-sulfur shift 81 Carbenium ions, stabilization 10 Carbon-carbon bond-forming reaction 35 Carbonyl vs. thiocarbonyl chemistry 25 Cephalosporin 114 Collidine 66 Cyclopropane 5 Cyclopropanethiocarboxamides 28 Cyclopropanethione 28 Dde Groot rearrangement 83 Dewar thiophene ligands 134 Diaryl disulfides 138 Dibromothiopropane 82 Difluoroiodotoluene 70 - 2, 3-Dihydro-l, 4-dithiine 84 Dihydro-1, 4-thiazine rearrangement 131 Dihydroisothianaphthene dioxide 21 Dihydropyrans 16 p-Dihydroquinones 52 Dihydrothiophene 130 Dimethyl sulfoxide 7 Dimethyl(methylthio)-sulfonium tetrafluoroborate (DMTSF) 10 - 1-Dimethylamino-naphthaline 23 Dimethyl-methylen-sulfurane 5 Diphenyldiazomethane 28 - 4, 4'-Di-tert-butyl-biphenyl, lithiated (LDBB) 23 - 1, 3-Dithiolanes, anionic cyclo... Domino reactions 45 EElectrophiles, non-carbon 11 Episulfide 130 Exomethylene 1, 4-dithiane 84 FFluorination reactions, Pummerer - reaction-initiated 69 - a-Fluorosulfides 69 Fredericamycin A 55 HHetarenes 3 Heterocycles, thio-substituted 79 Hexafluorothioacetone 26 IImidazolines 64 Indoles/indolenines 127 - 2, 3-O-Isopropylidene-D-glyceraldehyde 15 Isothiazolones 64 LLeaving group, sulfur 21 Linchpin chemistry 14 - 5-Lithiobenzofurans 57 - a -Lithiosulfoxides 66 - 2-Lithio-l, 3-thiazole 15 MMenthyl p-toluenesulfinate 17 Mesylate 129 Methyl p-tolyl sulfoxides 37 - S-Methyl-S-phenylsulfoximine 18 Morin rearrangement 77, 114 NNeolignans 57 OOrganometallic substrates 168 Organosulfur 1 Oxathiane, oxathioacetal ring expansion 84 Oxathioacetals 84 Oxidation states 9 Oxiranes 4 PPenicillin to cephalosporin 114 Perfluorination 92 Phenol ethers 52 Phenylsulfinylfurans 60 Pinacol 11 Polyoxamic acid 69 Pummerer reactions, asymmetric 48 - interrupted 63 Pummerer-type reactions, aromatic 52 Qo-Quinodimethane 21 Quinone O, S-acetals 53 RRadical sulfur migration 120 Ramberg-BÄncklund reaction 25 Ritter reaction 91 Rolliniastatin 38 SSelenium 29 Selenoxides 29 Shahamin K 11 2-Silylthioacetals 13 Sodium methylsulfinylmethylide 13 Sphingosines 69 - N-Sulfanylbenzimidazole derivatives 128 Sulfenamide 128 Sulfenic acids 8 Sulfides, chiral 6 - , cyclic 130 - , 1, 3-shift 125 Sulfilimines 9 Sulfimines 9 Sulfinic acids 8 Sulfinylimines, chiral 18 - 5-Sulfinylindoles 60 - p-Sulfinylphenols 52 - 2-Sulfinylthiophene 603-Sulfolenes 23 Sulfone, 1, 3-shift 125 Sulfonic acids 8 Sulfonium salts, organometallics 21 Sulfonyl migration, gem-disulfonyl - compounds 116 Sulfoxides, acyclic 143 - cyclic 146 - optically active, chiral auxiliaries/carbonyl equivalents 37 - 1, 3-shift 125 Sulfoximines 9, 15 Sulfoxonium ylides 5 - Sulfur, chiral 16 Sulfur migration 77 - carbenoid center 103 - carbohydrates 94 - elimination 81 - fragmentation/recombination 109 - heterocycles 100 - perfluorination 92 - radical 120 - Ritter reaction 91 - thiiranium intermediate 81 - thiirenium intermediate 104 - thioacetals 82 Sulfur shift, carbene 109 - carbocation 105 - sigmatropic [1, 5] 118 Sulfur ylides 4 - Sulfuranes 8 Superdienophiles 28 Superdipolarophiles 28 TTetrathiafulvalene 3 Thermolysis 135 Thia-Claisen 135 Thiadiazines 64 Thiamine (Vitamin B 1) 3 Thia-Payne rearrangement 99 Thiazetidines 133 Thiazines 133 Thiiranium 11, 77 - intermediates, addition of tethered nucleophiles 86 Thioacetals 82 - cyclic, ring expansion 110 - hydrolysis 12 Thioacetal S-oxide 7 Thioacetal S, S-dioxides 15 Thioacetal-supported domino process 14 Thioacylation 27 Thioamides 26 Thioanisole 10 Thiobutyrolactam 24 Thioketenes 26 Thione-enethiol tautomerism 27 Thionium ions 10 - , rearrangement 130 Thionocarbamates 26 Thionocarboxylic/thionocarbonic acid 26 Thiophene 3 Thiosulfonates 8 Thioureas 26 Tosylmethyl isocyanide 13 Total synthesis 35 Trithioorthocarboxylates 109 UUmpolung 14 VVinyl sulfone 21, 82 Vinyl sulfoxide 38 Vinyl thioethers 82 Vinyloxirane 5 YS-Ylides 4
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