INTRAMOLECULAR ADDITION OF ARYL RADICALS TO CARBON-NITROGEN DOUBLE-BONDS

Authors
GIOANOLA M LEARDINI R NANNI D PARESCHI P ZANARDI G
Citation
M. Gioanola et al., INTRAMOLECULAR ADDITION OF ARYL RADICALS TO CARBON-NITROGEN DOUBLE-BONDS, Tetrahedron, 51(7), 1995, pp. 2039-2054
Citations number
67
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
7
Year of publication
1995
Pages
2039 - 2054
Database
ISI
SICI code
0040-4020(1995)51:7<2039:IAOART>2.0.ZU;2-S
Abstract
Cyclisation of radicals 6a,b is highly regioselective towards a 5-exo process; 6-endo ring closure is a minor route and their ratio depends on the substituents. No ring expansion of tbe five-membered radical in termediates 7a,b was observed. Radicals 27a,b give rise to 5-exo cycli sation regiospecifically. A competitive 1,5-hydrogen shift leading to imidoyl radicals was noticed. An analogous behaviour is also exhibited by vinyl radicals when allowed to add to carbon-nitrogen double bonds .