Tetrahedron

Intramolecular addition of aryl radicals to carbon-nitrogen double bonds

M Gioanola, R Leardini, D Nanni, P Pareschi…

Index: Gioanola, Milena; Leardini, Rino; Nanni, Daniele; Pareschi, Patrizia; Zanardi, Giuseppe Tetrahedron, 1995 , vol. 51, # 7 p. 2039 - 2054

Full Text: HTML

Citation Number: 21

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 the five-membered radical intermediates 7a, b was observed. Radicals 27a, b give rise to 5-exo cyclisation 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 ...