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

RSC Advances Pub Date: 2014-12-15 DOI: 10.1039/C4RA09842K

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.

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