Nucleophilic reaction of glycidol tosylate and the corresponding cyclic sulfate with various nucleophiles: A comparative study

The nucleophilic reaction of glycidol tosylate and the corresponding cyclic sulfate tosylate have been carried out with a number of nucleophiles to study the possible attack of nucleophiles at C1, C2 or C3 positions. The regioselectivity and reactivity of both the substrates i.e. epoxide tosylate 1 and the corresponding cyclic sulfate 2 have been compared and established that under similar conditions cyclic sulfate counterpart shows better regioselectivity and better reactivity than the corresponding epoxide.