(Equation Presented) 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-Bu4NF, CrCl2, heat, and Lewis acids. They are readily removed by NalO4 or H2O2 in the presence of other common alcohol protecting groups.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry