N-(ORTHO-ARYLOXYPHENYL)ARYLIMIDOYL RADICALS - NOVEL 1,5-ARYL RADICAL TRANSLOCATION FROM OXYGEN TO CARBON

Authors
GUIDOTTI S LEARDINI R NANNI D PARESCHI P ZANARDI G
Citation
S. Guidotti et al., N-(ORTHO-ARYLOXYPHENYL)ARYLIMIDOYL RADICALS - NOVEL 1,5-ARYL RADICAL TRANSLOCATION FROM OXYGEN TO CARBON, Tetrahedron letters, 36(3), 1995, pp. 451-454
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
3
Year of publication
1995
Pages
451 - 454
Database
ISI
SICI code
0040-4039(1995)36:3<451:NR-N1R>2.0.ZU;2-K
Abstract
Imidoyl radicals 4a-d, obtained by hydrogen abstraction from imines 1a -d, give 7-membered cyclisation leading to oxazapines 2a-d. The interm ediate spirocyclohexadienyl radicals of the competitive 6-membered rin g closure (6a-d) rearrange to aryloxy radicals, giving benzophenones 3 a-d: the whole process entails a novel 1,5-aryl radical translocation from an oxygen to a carbon atom.