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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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4.2.1.8 Lewis acid-catalysed ketene dithioacetal
functionalization................................. 96
4.2.2 Thiophilic versus carbophilic addition of organometallics to
a C=S bond. Carbanions through thiophilic addition . . 96
4.2.2.1 Dithioesters........................................ 96
Thiophilic addition of Grignard reagents to methyl
dithioates............................................ 97
Egomaketone and perillene...............................100
Ethyl 3-furandithiocarboxylate........................... 101
Egomaketonedithioacetal................................. 101
Egomaketone............................................. 101
Perillene. ............................................. 101
4.2.2.2 Thionoesters, thioketones and thioaldehydes, and
thioamides....................................... 104
()-2-Ethyl-2-(methylthio)-8-hexyloxocane............... 104
()-cis-2-Ethyl-8-hexyloxocane (lauthisan)..............105
4.2.3 Reactions of enethiolates.................................. 106
4.2.4 The aldol reaction......................................... 107
Synthesis of methyl 3-oxodithioalkanoates...............109
(i) (i-Hydroxydithioesters............................. 109
(ii) fi-Oxodithioesters................................. 109
4.2.5 Michael addition........................................... 110
Michael addition of lithium enethiolates................ Ill
4.2.6 Alkylation of thioamides................................... 113
4.2.7 Thioesters and imidothioesters in C-C bond formation. . 113
One-pot thioimidoester-mediated synthesis of trans-(+)-a-atlantone................................... 116
4.2.8 Uses of sulfoxides......................................... 118
[}-Ketosulfoxides....................................... 120
Reduction of ketosulfoxides with DIBAH.................. 121
Reduction of ketosulfoxides with DIBAH in the presence
of ZnCl2................................................ 121
Oxidation of fRS)- and (RR)-(i-hydroxysulfoxides to
(S)- and (R)-sulfones................................... 121
Butenolides.............................................121
4.2.9 Use of sulfones............................................ 123
Desulfonylation of alkyl or vinyl phenyl sulfones . . . 124
4.3 C-C Bond-forming reactions..................................... 126
4.3.1 Use of sulfides and dithioacetals.......................... 126
4.3.2 Sulfone-based eliminations................................. 128
Preparation of an episulfone............................ 128
Alkenes by reductive elimination of fi-hydroxyimidazolyl
sulfones................................................ 130
2-(Benzenesulfonyl)tetrahydro-2H-pyran.................. 132
Condensation of the anion of
2-(benzenesulfonyl)tetrahydropyran with electrophiles 132 l,7-Dioxa[5.5]undecane 132
4.3.3 Carbonyl methylidenation with sulfoximines and other
derivatives............................................. 134
Alkenes from sulfoximines............................... 134
Alkenyl sulfides from thiolesters....................... 137
4.3.4 Two-fold extrusion......................................... 138
4.3.5 The Eschenmoser reaction................................... 140
Thiopyrrolidone......................................... 140
Alkylation of thiopyrrolidone with ethyl bromoacetate; preparation of an enamine ester......................... 140
4.3.6 Miscellaneous reactions..................................... 142
4.4 Three-membered ring-forming reactions. Cyclopropanation,
formation of epoxides.......................................... 143
4.4.1 Use of sulfur ylides........................................ 143
Trimethylsulfonium methyl sulfate....................... 143
Styrene oxide........................................... 144
Synthesis of epoxides from carbonyl compounds and
sulfonium salts........................................ 144
Synthesis ofbis(methylthio)dihydrofurans..............146
Conversion of bis(methylthio)dihydrofurans to
(methylthio)furans..................................... 146
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