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Sulfur reagents in organic - Metzner P.

Metzner P., Thuiller A. Sulfur reagents in organic - Academic press, 1994. - 200 p.
Download (direct link): sulfarreagents1994.djvu
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103
conversion to aldehydes 71,96 conversion to amides 111 conversion to esters 111 conversion to ketones 96 conversion to thioamides 111 cycloaddition with dienes 165 deprotunation of 98,106 Michael addition of 110-113 synthesis of 36-44
thiophilic addition with Grignard reagents 96-105 Dithiolanes cleavage of 14-18
Egomaketone 100 Egomaketonedithioacetal 101 Ene reaction 161 Enethiolates
as soft nucleophiles 106
Enethiols synthesis of 36 Episulfones 128 Epoxides synthesis of 143-147 Eschenmoser reaction 140 (±)-Estra- l,3,5(10)-triene- 17-one 178 (S)-Ethoxy p-tolyl vinyl sulfonium tetrafluoroborate 169 2-(Ethyldithio)hexadecanoic acid 11 Ethyl 3-furandithiocarboxylate 101 (±)-cw-2-Ethyl-8-hexyloxocane 105 (±)-2-Ethyl-2-(methjithio)-8-hexyloxocane
104
Ethyl 2-pyridyl disulfide 11
Fluorination 69-71
2-2(Furyl)-1,3-dithiane 13
synthesis by baker’s yeast reduction 102 đ-Hydroxy imidazolyl solfoncs 130 Đ-Hydroxy sulfoxides 121 P-Hydroxysulfoximines 134
Imidothioestcrs
aldol reaction of 117 alkylation of 115 deprotonation of 115 Michael addition to unsaturated derivatives of 116 reaction with Grignard and organolithium reagents 114 synthesis of 36,118 Ipso substitution 29 Isothiocyanates reaction with Grignard and organolithium reagents 42 synthesis of 49
Grignard reagents addition to thiolesters 114 reaction with alkenyl sulfides 94,146 reaction with carbon disulfide 40 reaction with dithioacetals 94 reaction with imidothioesters 114 reaction with isothiocyanates 42 reaction with sulfides 94 thiophilic addition to a thiocarbonyl group 96-105
H
Heimgartner reagent 32 1.4,7,11.14,17-Hexathiaicosane 9 Hydrogen sulfide as thiation reagent 32.34.36.43.44,103, 139
(5)-(+)-3-Hydroxy-4-
(benzyloxy)tris(methylthio)methane
80
P-Hydroxydithioesters reaction with organometallics 103 Swem oxidation of 109
Julia alkene synthesis 129
Ketenedithioacetals reaction with a carbenium ion 96 synthesis of 19-22,137 Ketones alkylidenation with sulfides 136 alkylidenation with sulfoxides 136 alkylidenation with sulfoximines 134 enatioselective reduction of 63 sulfenylation of 54,66 P-Ketosulfoxides 120 Kresze’s reagent 160
Lauthisan 105
Lawesson reagent 32,37-39,45,70,104 LDBB 90,92 LDM AN 90,92
M
(l/?.2S,5/?)-(-)-Menthyl (S)-p-toluenesulfinate 26 Methyl 3-hydroxy-4-benzyloxybulanoate 80 syn Methyl 2-(l-hydroxyethyl)-pent-4-enedithioate 157 Methyl 3-oxodithioalkanoates 109 Methyl 2-pyridinesulfinate 55 (Methylthio)furans 146 (/?)-(+)-Methyl p-tolyl sulfoxide 26 Michael addition of dithioacetal monoxide carbanions 81 of dithioester enethiolates 110-113 of sulfide carbanions 85 of sulfoxide carbanions 119 to unsaturated imidothioesters 116 to unsaturated sulfones 124 Mitsunobu reaction 4,125
Î
Organolithium reagents reaction with imidothioesters 114 reaction with isothiocyanates 42 reaction with non enethiolizable dithioesters 98 Orthotrithioesters 79 cleavage of 79 reaction with ketones 137 Oxathiane Eliel reagent 19 Oxaziridines as oxidising reagents 27 Oxiranes synthesis of 143-147 p-Oxodithioesters addition of organometallics to 102 baker’s yeast reduction of 102 synthesis of 109.117 Oxoketenedithioacetals reaction with ylides 145 synthesis of 19
P
Perillene 100
3-Phenylfuran 147
Phenyl 4-pentenedithioate 42 2-(Phenylthio)cyclooctanone 55 Phenylthiomethyllithium 86 Pummer reaction 64,81
R
Ramberg-Backlund reaction 128 Raney nickel 75,78,81,95,122,146 Reformatsky reaction of thiocarbonyl compounds 142 Retro-ene reaction 161
S
[2.3] Sigmatropic rearrangement 99.159
[3.3] Sigmatropic rearrangement 154 Stannanes 29
Styrene 29 Styrene oxide 144 (?')-Styryl p-tolyl sulfone 29 Sulfates
from diols 59 Sulfenylation of ketones 54,66 Sulfides
alkylidenation of ketones with 136 as alkylating agents 96 carbariiuris of 85, 89 desulfurization of 85 Hofmann elimination 126 oxidation of 23,28.95 reductive lithiation of 89-93 synthesis of 6-9 Sulfinamides alkylidenation of ketones with 136 use of chiral sulfinamides 27 Sulfinates 55 reaction with alkyl halides 28 use of chiral sulfinates 25 Sulfines 50 thiophilic addition with methyllithium 103 Sulfites chiral sulfoxides from 27 Sulfolenes 172-178 Suylfones alkylation of 123,125,174 cheletropic reaction of sulfolenes 172 conversion to ketones 72
[4+2] cycloaddition of unsaturated derivatives 170-172 desulfurization of 123,125 in alkene synthesis 128-133 Michael addition to unsaturated derivatives 124 oxidative desulfurization of 72 pyrolysis of 124,174 Rambcrg-Backlund reaction of 128 reaction of aldehydes 142 synthesis of 28-30 Sulfonium salts as alkylating agents [4+2] cycloaddition of unsaturated derivatives 168 sylfur ylides from 144 synthesis of 51.143 Sulfoxides alkylation of 138
alkylidenation of ketones with 136 [4+] cycloaddition of alkenyl derivatives 166 deprotonation of 118 in alcohol oxidation 62 in asymmetric reduction 63 in asymmetric synthesis 119-123,167 Michael addition of 119 oxidation to sulfones 120 Pummerer reaction of 64 pyrolysis of 95,133.166 reaction with esters 118,120 reaction with ketones 122 synthesis of 23-28 Sulfoximines 63 reaction with ketones 134 Sulfur
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