Substitution of α-Azido Sulfones with Thiolates to Form α-Azido Sulfides

Upon treatment of alpha-azido sulfones with a thiol in the presence of 1,1,3,3-tetramethylguanidine, substitution of the sulfonyl group with a thiolate occurred, resulting in the formation of alpha-azido sulfides. Based on experimental results and DFT calculations, a reaction mechanism that involves the addition of a thiolate to the azido group and generation of an alkylidene triazene is proposed.

Automated summary

Treatment of alpha-azido sulfones with a thiol in the presence of 1,1,3,3-tetramethylguanidine leads to the formation of alpha-azido sulfides through sulfonyl group substitution. Experimental and DFT calculations suggest a reaction mechanism involving thiolate addition to the azido group and generation of an alkylidene triazene.