HOMOLYTIC SUBSTITUTION BY IMINYL RADICAL AT SELENIUM - A FREE-RADICAL ROUTE TO 1,2-BENZOSELENAZOLES

被引：25
作者：
FONG, MC
SCHIESSER, CH
机构：
[1] DEAKIN UNIV,SCH BIOL & CHEM SCI,GEELONG,VIC 3217,AUSTRALIA
[2] UNIV MELBOURNE,SCH CHEM,PARKVILLE,VIC 3052,AUSTRALIA
来源：
TETRAHEDRON LETTERS | 1993年 / 34卷 / 27期
关键词：
HOMOLYTIC SUBSTITUTION; IMINYL RADICAL; 1,2-BENZOSELENAZOLES; SELENIUM; O-CARBOXYMETHYL OXIMES;
D O I：
10.1016/S0040-4039(00)79347-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Thiohydroxamic esters (3) derived from the O-carboxymethyl oxime derivatives (2) of 2-(benzylseleno)benzaldehyde (1:R = H), 2-(benzylseleno)acetophenone (1:R = Me) and 2-(benzylseleno)propiophenone (1:R = Et) decompose smoothly, upon irradiation, with the loss of carbon dioxide and formaldehyde to give the 1,2-benzoseknazoles (5). The reaction presumably involves the iminyl radical intermediate (4) which undergoes intramolecular free-radical homolytic substitution at selenium to afford the product (5).
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页码：4347 / 4348
页数：2
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