REACTIVITY OF SULFUR HETEROCYCLES

Abstract

The relationship between ring strain and the reactivity of alicyclic compounds has been of fundamental importance in the development of modern organic chemistry. Because of their biological interest, the reactivity and stereochemistry of cyclic phosphorus compounds have been extensively studied.^1,2 In recent years the reactivity of cyclic sulfur compounds has also begun to attract considerable interest. In 1966 it was pointed out that the common feature of sulfur-containing heterocycles is that nucleophilic attack at sulfur, be it di-, tri-, or tetra-coordinated, is always faster than the corresponding open-chain analogues.³ The present review attempts to discuss some fo the factors which affect the reactivity of cyclic sulfur compounds towards nucleophilic attack and to draw attention to some of the recently observed exceptions to this generalization.