Tetrahedron

New methods for reductive free-radical cyclizations of α-bromoacetals to 2-alkoxytetrahydrofurans with activated chromium (II)-acetate

C Hackmann, HJ Schäfer

Index: Hackmann, Claus; Schaefer, Hans J. Tetrahedron, 1993 , vol. 49, # 21 p. 4559 - 4574

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Citation Number: 42

Abstract

A method for the synthesis of γ-butyrolactones 6 is described in which the key step is a free- radical cyclization of α-bromoacetals 4 to 2-alkoxytetrahydrofurans 5 in 54–93% yield induced by activated chromium (II)-acetate. Four new methods have been developed in order to activate the transition metal. Two of them require only catalytic amounts of chromium (II)-acetate, because it can be regenerated in situ chemically or electrochemically. The ...