Novel triethylamine catalyzed S → O acetyl migration reaction to generate candidate thiols for construction of topological and functional sulfur-containing polymers

Abstract

We describe a novel triethylamine catalyzed S → O acetyl migration reaction for yielding thiol compounds under mild conditions through the formation of a transitional 5-membered ring. A series of epoxy compounds have been transformed into their thiol counterparts which could be used for construction of topological and functional sulfur-containing polymers. The one-pot two-step processes including the S → O acetyl migration and the following thiol-click reactions avoided separation of thiol intermediates. Applying these processes on a new-type latent polythiols overcomes crosslinking problem usually met in preparation of multithiol compounds due to the formation of disulfide bonds.