ChemInform Abstract: Ruthenium‐Catalyzed O‐ to S‐Alkyl Migration: A Pseudoreversible Barton—McCombie Pathway.

Abstract

Ap ractical ruthenium-catalyzed O-to S-alkyl migration affords structurally diverse thiooxazolidinones in excellent yields.O ur studies suggest this catalytic transformation proceeds through ap seudoreversible radical pathway drawing mechanistic parallels to the classic Barton-McCombie reaction.

Crystal structure of 3-(2-methylbenzyl)thiazolidin-2-one, C11H13ONS

“…The convenient synthesis of thiazolidinone derivatives has attracted much attention of synthetic chemists. Recently, the synthesis of thiazolidinone derivatives have been developed by ruthenium catalyzed O-to S-alkyl migration of N-alkyl oxazolidine-2-thiones via Barton-McCombie pathway [7]. However, the crystal structure of 3-(2-methylbenzyl)thiazolidin-2-one has not been reported until now.…”