Reaction of Dess-Martin periodinane with 2-(alkylselenyl)pyridines. Dehydration of primary alcohols under extraordinarily mild conditions: Tetrahedron Letters

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Abstract

Dess-Martin periodinane oxidizes very rapidly 2-pyridylseleno derivatives RR'CHCH2SePy in CHCl3 or CH2Cl2 and more chemoselectively than mCPBA. Tetravalent selenanes, RR'CHCH2Se(OAc)(2)Py, seem to be formed. Treatment of these intermediates with aqueous NaHCO3 gives rise to irreversible hydrolysis and elimination to terminal alkenes. As the OH/SePy exchange can be performed in minutes, the overall process is an exceptionally efficient procedure for the dehydration of primary alcohols. (C) 2010 Elsevier Ltd. All rights reserved.

Bibliographical metadata

Original languageEnglish
Pages (from-to)1863-1866
Number of pages4
JournalTetrahedron Letters
Volume51
DOIs
Publication statusPublished - 2010