SYNTHESIS OF PHENANTHRIDINES BY RADICAL C-ARYL-C-ARYL COUPLING

Citation
Am. Rosa et al., SYNTHESIS OF PHENANTHRIDINES BY RADICAL C-ARYL-C-ARYL COUPLING, Tetrahedron, 53(1), 1997, pp. 269-284
Citations number
34
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404020
Volume
53
Issue
1
Year of publication
1997
Pages
269 - 284
Database
ISI
SICI code
0040-4020(1997)53:1<269:SOPBRC>2.0.ZU;2-C
Abstract
Treatment of N-(o-bromobenzyl)anilines with 1-3 equivalent amounts of n-tributyltinhydride, in the presence of 0.5 to 0.6 mol equiv. of AIBN , results in the formation of phenanthridines in good yields. The mech anism of the oxidation step is probed with a deuterated aniline deriva tive and azobiscyclohexylcarbanonitrile (ABCN) as the initiator. It is shown that the carbon centred radical derived from the latter does no t act as the hydrogen abstracting species. Copyright (C) 1996 Elsevier Science Ltd