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Sulfur reagents in organic - Metzner P.

Sulfur reagents in organic

Author: Metzner P.
Other authors: Thuiller A.
Publishers: Academic press
Year of publication: 1994
Number of pages: 200
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Download: sulfarreagents1994.djvu

BEST SYNTHETIC METHODS
Sulfur
in Organic Synthesis
Patrick Metzner Andre Thuillier
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Detailed Contents
^ Introduction. . ........................... 1
2 Preparation of organosulfur reagents.................................... 3
2.1 Thiols.............................................................. 3
1.2-Benzenedithio l.................................... 3
‘ 2.2 Sulfides............................................................ 6
Thiolation of aldehydes and ketones: general procedure. 7
! Sulfides by addition of thiols to alkenes............... 8
1,4,7,11,14,17-Hexathiaicosane............................ 9
2.3 Disulfides and polysulfides......................................... 10
Ethyl 2-pyridyl disulfide............................... 11
2-(Ethyldithio)hexadecanoic acid........................ 11
Dimethyl trisulfide (R = Me).............................. 12
2.4 Thio- and dithioacetals and related compounds....................... 12
2-(2-Furyl)-l,3-dithiane................................ 13
Clay fen reagent........................................ 14
Cleavage of dithioacetals by clay-supported metal nitrates 15
Cleavage ofdithiolans by t-BuBr/DMSO.................... 16
Transthioacetalization with 4-nitrobenzaldehyde ... 16
Acyl silanes by anodic oxidation of
2-alkyl-2-trialkylsilyl-l,3-ditliiane s................. 17
Photolytic transformation of dithioacetals into carbonyl
compounds............................................... 18
2.5 Ketenedithioacetals and a-oxoketenedithioacetals.................... 19
Bis(dimethylaluminium) 1,3-propanedithiolate. ... 20
2-(3- Cyclohexenylidene)-l ,3-dithiane.................. 21
1,1-Bis(methylthio)-1,3-butadiene and
3-nwthyl-l,l-bis(methylthio)-l,3-butadiene .... 22
2.6 Sulfoxides.......................................................... 23
2.6.1 Oxidation of sulfides...................................... 23
1.3-Dithiane-l -oxide............................. 24
1.3-Dithiane-l, 1-dioxide............................... 24
2.6.2 Asymmetric synthesis of sulfoxides......................... 25
(lR,2S,5R)-(-)-Menthyl (S)-p-toluenesulfinate. ... 26
(R)-(+)-Methyl p-tolyl sulfoxide........................ 26
2.7 Sulfones............................................................ 28
(E)-Styryl p-tolyl sulfone.............................. 29
2.8 Thiocarbonyl compounds.............................................. 30
2.8.1 Thioaldehydes.............................................. 30
Silicon-assisted synthesis of thioaldehydes and trapping 31
2.8.2 Thioketones.................................................. 32
Di-t-butyl ketone imine................................. 33
Di-t-butyl thioketone................................... 34
(-)-Thiocamphor......................................... 34
2,6-Dimethylheptane-4-thione............................ 35
Selective synthesis of enethiols........................ 36
2.8.3 Thionoesters and dithioesters................................ 36
General procedure for the reactions of esters with
Lawesson’s reagent...................................... 38
Conversion of propanoic acid into methyl propanedithioate with Davy’s reagent (R2 = Me). . . 39
Preparation of dithioacetic acid by addition of methylmagnesium iodide to carbon disulfide. ... 40
General procedure for the preparation of dithioesters
from CS2 and Grignard reagents........................... 41
Phenyl 4-pentenedithioate................................ 42
Synthesis of saturated and unsaturated dithioesters through reaction of Grignard reagents with phenylisothiocyanate, alkylation and sulfhydrolysis . 43
2.8.4 Thioamides................................................... 44
N,N-Diethylthioacetamide................................. 45
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