ORTHO-SUBSTITUTED ARYL SULFOXIDES DESIGNED FOR HIGHLY DIASTEREOSELECTIVE RADICAL REACTIONS

被引:23
作者
RENAUD, P
BOURQUARD, T
机构
[1] Université de Fribourg, Institut de Chimie Organique
关键词
D O I
10.1016/0040-4039(94)88325-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Radical allylation of 1-arenesulfinylethyl radicals has been examined for different ortho-substituted aryl groups. High level of diastereoselectivity (up to 95 % ds) has been achieved with the o-chlorobenzenesulfinyl group. Rationalization of the results based on ground state conformation of the radicals is presented.
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收藏
页码:1707 / 1710
页数:4
相关论文
共 5 条
[1]   GROUND-STATES OF MOLECULES .48. MINDO-3 STUDY OF SOME RADICAL-ADDITION REACTIONS [J].
DEWAR, MJS ;
OLIVELLA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (17) :5290-5295
[2]   CRYSTAL AND MOLECULAR-STRUCTURES OF RING-SUBSTITUTED METHYL PHENYL SULFOXIDES - AN X-RAY AND MOLECULAR-ORBITAL ABINITIO INVESTIGATION [J].
IANELLI, S ;
MUSATTI, A ;
NARDELLI, M ;
BENASSI, R ;
FOLLI, U ;
TADDEI, F .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (01) :49-57
[3]   ADDITION OF SULFINYLATED AND SULFONYLATED CARBON CENTERED RADICALS TO ALKENES AND ENOLETHERS [J].
RENAUD, P .
TETRAHEDRON LETTERS, 1990, 31 (32) :4601-4604
[4]  
RENAUD P, TETRAHEDRON LETT
[5]  
TSAI YM, 1990, TETRAHEDRON LETT, V31, P6047