DETECTION AND DECOMPOSITION OF DI-TERT-BUTYL DISULFIDE-POLYOXIDE DERIVATIVES

被引:20
作者
DERBESY, G [1 ]
HARPP, DN [1 ]
机构
[1] MCGILL UNIV,DEPT CHEM,MONTREAL,PQ H3A 2K6,CANADA
关键词
D O I
10.1021/jo00109a042
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The chemistry of di-tert-butyl disulfide polyoxide derivatives has been investigated. Low-temperature experiments permit the clear detection of vic-disulfoxides (alpha-disulfoxides). In addition, a proposal for a decomposition mechanism that accounts for the detection of one of the diastereoisomers and the formation of the final products has been advanced. The formation of di-tert-butyl thiosulfonate was also shown to be solvent and concentration dependent. Finally, low-temperature experiments permit the detection of the sulfinyl sulfone and vic-disulfone derivatives. A general mechanism has been proposed for the decomposition of these disulfide polyxoide derivatives.
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页码:1044 / 1052
页数:9
相关论文
共 49 条
[11]  
DERBESY G, 1994, THESIS MCGILL U
[12]   SUBSTITUTION-REACTIONS OF ALKANESULFONYL DERIVATIVES - DIRECT SUBSTITUTION VS ELIMINATION-ADDITION MECHANISMS IN SUBSTITUTION-REACTIONS OF ALKYL ALPHA-DISULFONES [J].
FARNG, LO ;
KICE, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (05) :1137-1145
[13]   ALPHA-DISULFOXIDES AND OTHER INTERMEDIATES IN THE OXIDATION OF DISULFIDES [J].
FOLKINS, PL ;
HARPP, DN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (08) :3066-3070
[14]   CLEAR EVIDENCE FOR THE FORMATION OF ALPHA-DISULFOXIDES AND OTHER INTERMEDIATES IN THE META-CPBA OXIDATION OF BRIDGED BICYCLIC THIOSULFINATES [J].
FOLKINS, PL ;
HARPP, DN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8998-9000
[15]   VIC-DISULFOXIDES AND OS-SULFENYL SULFINATES [J].
FREEMAN, F .
CHEMICAL REVIEWS, 1984, 84 (02) :117-135
[16]   C-13 NUCLEAR MAGNETIC-RESONANCE STUDY OF THE CONFORMATIONS OF DISULFIDES AND THEIR OXIDE DERIVATIVES [J].
FREEMAN, F ;
ANGELETAKIS, CN .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (22) :4194-4200
[17]   AN ABINITIO MOLECULAR-ORBITAL STUDY OF THE REARRANGEMENT OF ALPHA-DISULFOXIDE TO THIOSULFONATE [J].
FREEMAN, F ;
ANGELETAKIS, CN ;
PIETRO, WJ ;
HEHRE, WJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (05) :1161-1165
[18]   C-13 NMR AND H-1-NMR CHEMICAL-SHIFTS OF BIS(1,1-DIMETHYLETHYL) DISULFIDE AND BIS(1,1-DIMETHYLETHYL) TRISULFIDE AND THEIR OXIDE DERIVATIVES [J].
FREEMAN, F ;
LEE, CS .
MAGNETIC RESONANCE IN CHEMISTRY, 1988, 26 (09) :813-816
[19]   FORMATION OF SULFINES IN THE PEROXYACID OXIDATION OF NEOPENTYL NEOPENTANETHIOSULFINATE [J].
FREEMAN, F ;
ANGELETAKIS, CN ;
MARICICH, TJ .
TETRAHEDRON LETTERS, 1981, 22 (20) :1867-1870
[20]   FORMATION OF ALPHA-DISULFOXIDES, SULFINIC ANHYDRIDES, AND SULFINES DURING THE META-CHLOROPEROXYBENZOIC ACID OXIDATION OF SYMMETRICAL S-ALKYL ALKANETHIOSULFINATES [J].
FREEMAN, F ;
ANGELETAKIS, CN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (12) :4039-4049