Tetrahedron

The invention of new radical chain reactions: part XIII. Generation and reactivity of perfluoroalkyl radicals from thiohydroxamic esters

DHR Barton, B Lacher, SZ Zard

Index: Barton, Derek H. R.; Lacher, Brigitte; Zard, Samir Z. Tetrahedron, 1986 , vol. 42, # 8 p. 2325 - 2328

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Citation Number: 29

Abstract

The perfluoro acid esters of N-hydroxypyridine 2-thione give perfluoroalkyl radicals on irradiation. Without any trap the radicals participate in a decarboxylative rearrangement to give 2-perfluoroalkylthiopyridines in excellent yield. In the presence of an appropriate trap, such as an electron rich olefin, adducts are formed in variable yield.