Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols
Moshood O. Ganiu, Alexander H. Cleveland, Jarrod L. Paul, Rendy Kartika*
*Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, United States,
Email: rkartika
lsu.edu
M. O. Ganiu, A. H. Cleveland, J. L. Paul. R. Kartika, Org. Lett., 2019, 21, 5611-5615.
DOI: 10.1021/acs.orglett.9b01959
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Abstract
The combination of triphosgene and DMAP enables a chemoselective dehydration of tertiary alcohols in DCM at room temperature. This reaction tolerates a broad scope of substrates, yielding alkenes preferentially with (E)-geometry. While formation of the Hofmann products is generally favored, selectivity toward the Zaitzev products is observed when the reaction is carried out in DCE at reflux.
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proposed mechanism
Key Words
cyclohexenes, eliminations, Hofmann rule
ID: J54-Y2019
