Tetrahedron letters

Aryl pyrrolidinones via radical 1, 4-aryl migration and 5-endo-trig cyclisation of N-(2-bromoallyl) arylcarboxamides

MJ Palframan, K Tchabanenko, J Robertson

Index: Palframan, Matthew J.; Tchabanenko, Kirill; Robertson, Jeremy Tetrahedron Letters, 2006 , vol. 47, # 47 p. 8423 - 8425

Full Text: HTML

Citation Number: 12

Abstract

Radical reaction of a series of N-(2-bromoallyl) arylcarboxamides led to the production of 4- arylpyrrolidin-2-ones and directly reduced materials in comparable yields. A cascade process, involving sequential 5-exo-trig spirocyclisation, β-scission, and 5-endo-trig cyclisation of the resulting acyl radical, is proposed to explain the pyrrolidinone products.