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.
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页码：4393 / 4401
页数：9
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