FRAGMENTATION OF ALKOXY RADICALS - TANDEM BETA-FRAGMENTATION-CYCLOPEROXYIODINATION REACTION

被引：31

作者：

BOTO, A

BETANCOR, C

PRANGE, T

SUAREZ, E

机构：

[1] CSIC,INST PROD NAT & AGROBIOL,E-38206 LA LAGUNA,SPAIN

[2] UNIV LA LAGUNA,DEPT QUIM ORGAN,LA LAGUNA,SPAIN

[3] UNIV PARIS 11,LURE,F-91405 ORSAY,FRANCE

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 16期

关键词：

D O I：

10.1021/jo00095a012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The steroidal alcohols 2-cholesten-5 alpha-ol (3), 3-phenyl-2-cholesten-5 alpha-ol (4), and 3 alpha H-2'-oxofuro-[2,3]cholestan-5 alpha-ol (5) were prepared in order to test a new tandem beta-fragmentation-cycloperoxyiodination reaction. The alkoxy radicals generated by irradiation of these alcohols with visible light in the presence of (diacetoxyiodo)benzene, I-2, and molecular oxygen undergo a beta-fragmentation reaction with subsequent peroxidation of the C-radical formed. This peroxy radical is added to conveniently positioned double bonds to give 10-membered cyclic ketones possessing a 1,2-dioxolane group.

引用

页码：4393 / 4401

页数：9

共 61 条

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