STEREOCHEMISTRY OF THE C-S BOND-CLEAVAGE IN 1-PHENYLETHYL PHENYL SULFIDE RADICAL-CATION - EVIDENCE FOR A UNIMOLECULAR PATHWAY

被引:28
作者
BACIOCCHI, E [1 ]
FASELLA, E [1 ]
LANZALUNGA, O [1 ]
MATTIOLI, M [1 ]
机构
[1] CNR,CTR STUDIO MECCANISMI REAZ,ROME,ITALY
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1993年 / 32卷 / 07期
关键词
D O I
10.1002/anie.199310711
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Is the bond-cleavage mechanism uni- or bimolecular in the reaction (a)? The search for the answer involved the use of enantiomerically pure (R)-(+)-1, reaction conditions with or without base, and detailed product analyses. The experimental results are consistent with a unimolecular pathway, which initially leads to a contact radical cation pair and then to a solvent-separated radical cation pair.
引用
收藏
页码:1071 / 1073
页数:3
相关论文
共 26 条
[1]  
ALBINI A, 1988, PHOTOINDUCED ELECT C, pCH3
[2]   MEDIUM AND STRUCTURE EFFECTS ON THE ANODIC-OXIDATION OF ARYL ARYLMETHYL SULFIDES [J].
BACIOCCHI, E ;
ROL, C ;
SCAMOSCI, E ;
SEBASTIANI, GV .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19) :5498-5502
[3]   SIDE-CHAIN REACTIVITY OF AROMATIC RADICAL CATIONS [J].
BACIOCCHI, E .
ACTA CHEMICA SCANDINAVICA, 1990, 44 (07) :645-652
[4]   A KINETIC-STUDY OF THE ELECTRON-TRANSFER-INITIATED CARBON SILICON BOND-CLEAVAGE REACTIONS OF BENZYLTRIALKYLSILANES PROMOTED BY 12-TUNGSTOCOBALT(III)ATE ION [J].
BACIOCCHI, E ;
CRESCENZI, M ;
FASELLA, E ;
MATTIOLI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (17) :4684-4689
[5]  
BACIOCCHI E, 1989, GAZZ CHIM ITAL, V119, P649
[6]  
BACIOCCHI E, 1988, PHOTOINDUCED ELECT C
[7]  
CAREY FA, 1977, ADV ORGANIC CHEM, pCH5
[8]  
CI X, 1988, PHOTOINDUCED ELECT C, pCH9
[9]   NUCLEOPHILE-ASSISTED CLEAVAGE OF SILANE CATION RADICALS [J].
DINNOCENZO, JP ;
FARID, S ;
GOODMAN, JL ;
GOULD, IR ;
TODD, WP ;
MATTES, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (24) :8973-8975
[10]   PHOTOOXIDATIVE CLEAVAGE OF ORGANOSILANES [J].
DINNOCENZO, JP ;
FARID, S ;
GOODMAN, JL ;
GOULD, IR ;
TODD, WP .
MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1991, 194 :151-157