Direct observation of a carbene-alcohol ylide

J Am Chem Soc. 2011 Feb 16;133(6):1763-5. doi: 10.1021/ja111029g. Epub 2011 Jan 25.

Abstract

Carboethoxycarbene reacts with methanol-OD to form an ylide. The formation and decay of this ylide was monitored by ultrafast time-resolved IR spectroscopy. The formation and decay of the ylide is linearly dependent on the concentration of methanol-OD in acetonitrile with second-order rate constants of ylide formation (8.4 × 10(9) M(-1) s(-1)) and decay (1.4 × 10(9) M(-1) s(-1)). Similar results were obtained with 1-butanol.