THE PHOTOCHEMISTRY OF ACYL AZIDES .9. DIRECT AND SENSITIZED PHOTOLYTIC GENERATION OF ACYLNITRENES FOR CYCLOADDITION REACTIONS

Authors
CLAUSS KU BUCK K ABRAHAM W
Citation
Ku. Clauss et al., THE PHOTOCHEMISTRY OF ACYL AZIDES .9. DIRECT AND SENSITIZED PHOTOLYTIC GENERATION OF ACYLNITRENES FOR CYCLOADDITION REACTIONS, Tetrahedron, 51(26), 1995, pp. 7181-7192
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
26
Year of publication
1995
Pages
7181 - 7192
Database
ISI
SICI code
0040-4020(1995)51:26<7181:TPOAA.>2.0.ZU;2-0
Abstract
Contrary to ethoxycarbonylnitrene, selective reactions - including cyl oadditions - can be carried out with benzoylnitrene. This study analyz es the sequence of reactivity of various bond types with respect to be nzoylnitrene, which was generated by three different routes: direct ph otolysis of benzoyl azide, sensitization of azide decomposition via en ergy transfer, and photoinduced electron transfer. In all cases the sa me cycloadducts 23, 24, and 30 were obtained. Carbonyl activity determ ines the reactivity of unsaturated ketones and aldehydes with respect to benzoylnitrene.