FRAGMENTATION OF ALKOXY RADICALS AND OXIDATIVE ELIMINATION OF ALICYCLIC IODIDES

被引：43

作者：

LEE, JH ^{[1
]}

OH, JH ^{[1
]}

JIN, SJ ^{[1
]}

CHOI, JR ^{[1
]}

ATWOOD, JL ^{[1
]}

CHA, JK ^{[1
]}

机构：

[1] UNIV ALABAMA,DEPT CHEM,TUSCALOOSA,AL 35487

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 23期

关键词：

D O I：

10.1021/jo00102a019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The azaallyl cation-mediated [4 + 3] cycloaddition with spiro[2.4]hepta-4,6-diene by the procedure of Schmid provides the tricyclic cycloadducts of general type 3. The keto bridge of the cycloadducts 17c, 21, and 22 has been cleaved by PhI(OAc)(2)-I-2 (Suarez cleavage), which involves P-fragmentation of an alkoxy radical, to furnish iodo lactones 19, 32, and 30a,b, respectively. Subsequent oxidation of these alkyl iodides has been investigated to develop a new synthetic route for bridgehead olefins (i.e., 33) of medium-sized carbocycles.

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收藏

页码：6955 / 6964

页数：10

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