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).

引用

页码：4347 / 4348

页数：2

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