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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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3-Phenylfuran.......................................... 147
4.4.2 Helquist cyclopropanation with iron-bonded sulfonium
ylides................................................. 149
Cyclopropanation of 1,1 -diphenylethene with Helquist’s reagent................................................. 149
4.4.3 Cyclopropanation with t-butylsulfonyl methyllithium . . 150
Cyclopropanation of alkenes with sulfonyl carbanions . 151
4.4.4 Asymmetric synthesis with sulfur ylides.................... 152
Cyclopropanation of methyl
3,3-diphenyl-2-(Tp-tolylsulfinyl)-2-propenoate . . . 153
4.5 Pericyclic reactions of organosulfur compounds.................. 153
4.5.1 The thio-Claisen rearrangement.............................. 154
syn-Methyl 2-(l-hydroxyethyl)-pent-4-enedithioate by the
thio-Claisen rearrangement..............................157
Ketene Claisen rearrangement of an allylthioether. . . 158
4.5.2 [2,3] Sigmatropic processes................................. 159
4.5.3 Ene and retro-ene reactions................................. 161
4.5.4 Cycloaddition reactions.................................... 163
(±)-2-(l-t-Butyl-2,2-dimethylpropylidene)bornene . . 164
4.5.4.1 Thiocarbonyl compounds in (4 + 2) cycloaddition . 164
4.5.4.2 Ancillary role of sulfur functionalities in
cycloaddition reactions........................... 166
(a) Vinyl sulfides................................ 166
(b) Vinyl sulfoxides.............................. 167
(S)-Ethoxy p-tolyl vinyl sulfonium
tetrafluoroborate............................ 169
Diels-Alder reaction with cyclopentadiene . . 169
(c) Vinyl sulfones................................ 170
4.5.5 Cheletropic processes...................................... 172
3,6-Diethyl-3,5-octadiene from a sulfolene............. 174
2-Tributylstannyl-2,5-dihydrothiophene-S-S-dioxide. . 177
(E)-l,3-Butadienyl(tributyl)stannane................... 177
(±)-Estra-l,3,5(10)-triene-17-one...................... 178
Abbreviations
Ac acetyl
acac acetylacetonate
AIBN azobis(isobutyronitrile)
9-BBN 9-borabicyclo[3.3.1]nonane
BTSP bis(trimethylsilyl)peroxide
Bu butyl
Cp cyclopentadienyl
m-CPBA m-chloroperoxybenzoic acid
DABCO l,4-diazabicyclo[2.2.2]octane
DAST diethylaminosulfur trifluoride
DBB di-t-butylbiphenyl
DBH l,3-dibromo-5,5-dimethylhydantoin
DBIJ l,8-diazabicyclo[5.4.0]undec-7-ene
DCC 1,3-dicyclohexylcarbodiimide
DIBAH diisobutylaluminium hydride
DITOX 1,3-dithiane-1 -oxide
DMAP 4-dimethylaminopyridine
DMDS dimethyl disulfide
DMF 7V,N-dimethylformamide
DMSO dimethyl sulfoxide
DMSY dimethyl sulfoxonium ylide
dppe l,2-bis(diphenylphosphino)ethane
EE ethoxyethyl
Et ethyl
FAMSO formaldehyde dimethyl dithioacetal 5-oxide (=MMTS)
GC/MS gas chromatography/mass spectroscopy
GLC gas-liquid chromatography
HMPA hexamethylphosphoramide
HPLC high-pressure liquid chromatography
Imid imidazolyl
LDA lithium diisopropylamide
LDBB lithium p,p' -di-tert-butylbiphenylide
LDMAN lithium 1 -(dimethylamino)naphthalenide
LHMDS lithium hexamethyldisililazide
LR Lawesson reagent
Me methyl
xviii ABB
MMTS methyl methylthiomethyl sulfoxide (=FAMSO)
MsOH methanesulfonic acid
NBS /V-bromosuccinimide
NHMDS sodium hexamethyldisililazide
NMP N-methyl-2-pyrrolidone
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