TANDEM RADICAL [2- REMARKABLE SILYL SUBSTITUENT EFFECT ON THE CHEMOSELECTIVITY OF THE RADICAL CYCLIZATION REACTIONS(1] CYCLOADDITION )

Authors
WENG WW LUH TY
Citation
Ww. Weng et Ty. Luh, TANDEM RADICAL [2- REMARKABLE SILYL SUBSTITUENT EFFECT ON THE CHEMOSELECTIVITY OF THE RADICAL CYCLIZATION REACTIONS(1] CYCLOADDITION ), Journal of organic chemistry, 58(21), 1993, pp. 5574-5575
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
58
Issue
21
Year of publication
1993
Pages
5574 - 5575
Database
ISI
SICI code
0022-3263(1993)58:21<5574:TR[RSS>2.0.ZU;2-8
Abstract
Tandem radical cyclization of bromides 1 with Bu3SnH is extremely sens itive to the nature of the substituent on the diene moiety. Bicyclo[3. 1.0] skeleton 3 is obtained in the presence of the silyl substituent. The tert-butyl substituent gives exclusively six-membered ring product s 15. Tributyltin radical addition to the double bond becomes predomin ant when the substituent is phenyl.