Title of article
Reaction of Dess–Martin periodinane with 2-(alkylselenyl)pyridines. Dehydration of primary alcohols under extraordinarily mild conditions
Author/Authors
Andreou، نويسنده , , Thanos and Burés، نويسنده , , Jordi and Vilarrasa، نويسنده , , Jaume، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2010
Pages
4
From page
1863
To page
1866
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)2Py, 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.
Keywords
Pyridylselenanes , Terminal double bonds
Journal title
Tetrahedron Letters
Serial Year
2010
Journal title
Tetrahedron Letters
Record number
1871666
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