Tetrahedron

Radical 1, 4-aryl transfer in arylcarboxamides leading to phthalimides, biaryls and enantiomerically enriched β-arylethylamines

J Robertson, MJ Palframan, SA Shea, K Tchabanenko…

Index: Robertson, Jeremy; Palframan, Matthew J.; Shea, Stephen A.; Tchabanenko, Kirill; Unsworth, William P.; Winters, Chase Tetrahedron, 2008 , vol. 64, # 52 p. 11896 - 11907

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Citation Number: 14

Abstract

5-exo Cyclisation of vinyl-, aryl-and alkyl-radicals onto the aryl group of arylcarboxamides is followed by β-scission of the resulting spirocyclohexadienyl radicals with ejection of a carbamoyl radical. The fate of this radical depends on the substrate but, in the cases studied, either 5-endo cyclisation or direct reduction follows to give phthalimides, biaryls or β- arylethylamines.

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