Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols
Copyright © 2019 American Chemical Society. The utility of triphosgene and DMAP as mild reagents for chemoselective dehydration of tertiary alcohols is reported. Performed in dichloromethane at room temperature, this reaction is readily tolerated by a broad scope of substrates, yielding alkenes preferentially with the (E)-geometry. While formation of the Hofmann products is generally favored, a dramatic change in alkene selectivity toward the Zaitzev products is observed when the reaction is carried out in dichloroethane at reflux.
Publication Source (Journal or Book title)
Ganiu, M., Cleveland, A., Paul, J., & Kartika, R. (2019). Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols. Organic Letters, 21 (14), 5611-5615. https://doi.org/10.1021/acs.orglett.9b01959