Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols
Moshood O Ganiu1, Alexander H Cleveland1, Jarrod L Paul1
1Department of Chemistry , Louisiana State University , 232 Choppin Hall , Baton Rouge , Louisiana 70803 , United States.
Abstract:
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.
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