The Journal of Organic Chemistry

Diiodosilane. 3. Direct synthesis of acyl iodides from carboxylic acids, esters, lactones, acyl chlorides and anhydrides

E Keinan, M Sahai

Index: Keinan, E.; Sahai, M. Journal of Organic Chemistry, 1990 , vol. 55, # 12 p. 3922 - 3926

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Citation Number: 12

Abstract

Diiodosilane (SiH212, DIS) is a very useful reagent for direct, high-yield synthesis of acyl iodides from variety of carboxylic acid derivatives, such as carboxylic acids, esters, lactones, anhydrides, and acyl chlorides. These transformations are remarkably accelerated by iodine. In the absence of iodine DIS reacts with carboxylic acids and esters, much as does iodotrimethylsilane (TMSI), to form the corresponding silyl carboxylates. However, in ...