Steric and electronic effects of secondary alcohols on reaction with Martin's sulfurane

ORGN 98

Madeline A. Weber, mweber@bates.edu and Jennifer L. Koviach-Côté. Department of Chemistry, Bates College, 5 Andrews Rd., Lewiston, ME 04274
Upon treatment with Martin's sulfurane, secondary alcohols typically undergo dehydration. However, we recently found that under the same conditions, a propargylic alcohol did not afford the expected olefin, but instead underwent an unprecedented oxidation. We present here a study of the steric and electronic effects of secondary alcohols on reaction with Martin's sulfurane.