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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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2.8.5 Xanthates .................................................... 46
Synthesis ofO-alkyl S-methyl dithiocarbonates (xanthates) 47
2.8.6 Miscellaneous thiocarbonyl compounds.......................... 48
2.8.6.1 Thioketenes........................................ 48
2.8.62 Isothiocyanates.................................... 49
Cyclohexyl isothiocyanate................................ 49
2.8.6.3 Sulfines and sulfenes.............................. 50
2.9 Sulfonium salts and sulfur ylides................................ 51
3 Functional modifications with organosulfur compounds................... 53
3.1 Introduction of unsaturation..................................... 53
3.1.1 Creation of a double bond a to a carbonyl group. ... 54
Oxidation of diphenyl disulfide with chloramine . . 54
2-(Phenylthio)cyclooctanone.............................. 55
Methyl 2-pyridinesulfinate............................... 55
Sulfinylation of ketones and elimination................. 57
3.1.2 Alkenes from 1,2-dihalo compounds............................. 57
Dehydrohalogenation of meso-l,2-dibromo-l,2-diphenylethane...................... 57
3.1.3 Alkenes from 1,2-diols........................................ 58
Alkenes from vic-dixanthates............................. 59
3.2 Radical deoxygenation of alcohols: the Barton reaction ... 60
Cholestane from a cholestanol thionocarbonate ... 61
3.3 Oxidation of alcohols............................................ 62
3.4 Asymmetric reduction............................................. 63
3.4.1 Sulfinyl-induced asymmetric reduction......................... 63
3.4.2 0-Hydroxysulfoximine-catalysed enantioselective
reduction of ketones..................................... 63
3.5 Decarboxylation................................................... 64
3.6 The Pummerer rearrangement........................................ 64
(7R,5R )-6,6-Dimethyl-3- (phenylthio) bicyclo[3.1.1 Jhept-
Η-εο-2-ξοε 66
3.7 Miscellaneous reactions........................................... 67
Deracemization of a terpenic thiolester.................. 69
Fluorination of methyl arenedithiocarboxylates. ... 69
Fluorination of thionesters with DAST.................... 71
Conversion ofsulfones to aldehydes or ketones. ... 73
4 Organosulfur compounds as intermediates in organic synthesis . . 75
4.1 A word on desulfurization......................................... 75
4.2 C-C bond-forming reactions........................................ 75
4.2.1 Use of sulfides, dithioacetals and orthotrithioesters . . . 75
4.2.1.1 1,3-Dithianes as acyl anion equivalents .... 75
Ring opening ofaziridine with dithianes.................. 77
Hydrolytic removal ofdithiane............................ 77
Propyl cyclopentyl ketone (via a borate complex of
lithiobenzodithiole).................................. 79
4.2.1.2 Carboxy anion equivalents........................... 79
(S)-(+)-3-Hydroxy-4- (benzyloxy)tris (methylthio )methane 80
Methyl 3-hydroxy-4-benzyloxybutanoate.................... 80
4.2.1.3 Thioacetal monoxides................................ 81
Synthesis of an amino ester.............................. 82
4.2.1.4 a-Metallated sulfides............................... 85
Preparation of a solution of phenylthiomethyllithium 86
Bis(phenylthio)methyllithium............................. 87
4.2.1.5 Reductive lithiation of phenyl sulfides............. 89
Lithium p,p '-di-tert-butylbiphenylide (LDBB). ... 92
Cyclohexenyllithium by metallation of
phenylthiocyclohexene................................. 92
Cyclohexenyl cyclohexyl methanol......................... 92
4.2.1.6 Metal-catalysed Grignard reaction with sulfides
and dithioacetals ................................ 94
Camphene synthesis via gem-dimethylation of a dithiolane 94
4.2.1.7 Reactions of a-halo sulfides with silyl enolates . . 95
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