Tetrahedron

β-Functionalised radicals in organic synthesis: 2-acyloxyalkyl radicals from 2-acyloxyalkyl iodides by the tin route

F Foubelo, F Lloret, M Yus

Index: Foubelo, Francisco; Lloret, Francisco; Yus, Miguel Tetrahedron, 1994 , vol. 50, # 17 p. 5131 - 5138

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Citation Number: 3

Abstract

The reaction of iodoesters 1a-c with electrophilic olefins 2a-d and in situ generated tributyltin hydride (from a substoichiometric amount of tributyltin chloride and an excess of sodium borohydride) in the presence of a catalytic amount of AIBN in ethanol at 0 to 20° C yields the expected coupling products 3aa-3cd. Products 4 resulting from an iodine/hydrogen exchange are also obtained as by-products in variable amounts. The stereochemistry of ...