Title

Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols

Document Type

Article

Publication Date

6-28-2019

Abstract

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)

Organic Letters

First Page

5611

Last Page

5615

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