FRAGMENTATION OF ALKOXY RADICALS AND OXIDATIVE ELIMINATION OF ALICYCLIC IODIDES

Authors
LEE JH OH JH JIN SJ CHOI JR ATWOOD JL CHA JK
Citation
Jh. Lee et al., FRAGMENTATION OF ALKOXY RADICALS AND OXIDATIVE ELIMINATION OF ALICYCLIC IODIDES, Journal of organic chemistry, 59(23), 1994, pp. 6955-6964
Citations number
71
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
59
Issue
23
Year of publication
1994
Pages
6955 - 6964
Database
ISI
SICI code
0022-3263(1994)59:23<6955:FOARAO>2.0.ZU;2-2
Abstract
The azaallyl cation-mediated [4 + 3] cycloaddition with spiro[2.4]hept a-4,6-diene by the procedure of Schmid provides the tricyclic cycloadd ucts of general type 3. The keto bridge of the cycloadducts 17c, 21, a nd 22 has been cleaved by PhI(OAc)(2)-I-2 (Suarez cleavage), which inv olves P-fragmentation of an alkoxy radical, to furnish iodo lactones 1 9, 32, and 30a,b, respectively. Subsequent oxidation of these alkyl io dides has been investigated to develop a new synthetic route for bridg ehead olefins (i.e., 33) of medium-sized carbocycles.