ABNORMALLY HIGH REACTIVITY OF THE VINYL HYDROGEN TOWARD SINGLET OXYGEN IN A TWISTED 1,3-DIENE

Authors
MORI H IKOMA K MASUI Y ISOE S KITAURA K KATSUMURA S
Citation
H. Mori et al., ABNORMALLY HIGH REACTIVITY OF THE VINYL HYDROGEN TOWARD SINGLET OXYGEN IN A TWISTED 1,3-DIENE, Tetrahedron letters, 37(43), 1996, pp. 7771-7774
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
43
Year of publication
1996
Pages
7771 - 7774
Database
ISI
SICI code
0040-4039(1996)37:43<7771:AHROTV>2.0.ZU;2-K
Abstract
In a significantly twisted 1,3-diene, a regio-selective ene-reaction o f the vinyl hydrogen rather than the allyl hydrogen with singlet oxyge n was observed, and this phenomena is rationalized by considering larg e sigma-pi orbital interactions between the vinyl C-H bond and anothe r double bond. Copyright (C) 1996 Elsevier Science Ltd.