Organic Letters 2003-12-11

Dimethylthiocarbamate (DMTC): an alcohol protecting group.

D K Barma, A Bandyopadhyay, Jorge H Capdevila, J R Falck

Index: Org. Lett. 5(25) , 4755-7, (2003)

Full Text: HTML

Abstract

Dimethylthiocarbamates (DMTCs), prepared from the corresponding alcohols using commercial dimethylthiocarbamoyl chloride, are spectrally simple, achiral, and nonpolar. DMTCs are moderately to highly stable to a wide range of reagents and conditions including metal hydrides, hydroboration, ylides, NaOH, HCl, organolithiums, Grignards, DDQ, PCC, Swern, n-Bu(4)NF, CrCl(2), heat, and Lewis acids. They are readily removed by NaIO(4) or H(2)O(2) in the presence of other common alcohol protecting groups. [structure: see text]