1,4-RADICAL ELIMINATION IN CYCLOHEXANE SYSTEMS - A MODEL FOR THE CHORISMATE SYNTHASE REACTION

Authors
GIESE B ALMSTEAD NG
Citation
B. Giese et Ng. Almstead, 1,4-RADICAL ELIMINATION IN CYCLOHEXANE SYSTEMS - A MODEL FOR THE CHORISMATE SYNTHASE REACTION, Tetrahedron letters, 35(11), 1994, pp. 1677-1680
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
11
Year of publication
1994
Pages
1677 - 1680
Database
ISI
SICI code
0040-4039(1994)35:11<1677:1EICS->2.0.ZU;2-P
Abstract
Treatment of cyclohexenyl bromide 9 with low concentration of Bu(3)SnH gives cyclohexadiene 10 via allylic radical 14 as intermediate. This 1,4 radical elimination is a model reaction of the conversion of shiki mate 1 to chorismate 4. Kinetic studies show that the elimination step from allyl radical 14 to cyclohexadiene 10 is relatively slow.