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

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• 作者：Thanos Andreou ; Jordi Buré ; s ; Jaume Vilarrasa
• 关键词：Pyridylselenanes ; Terminal double bonds
• 刊名：Tetrahedron Letters
• 出版年：2010
• 出版时间：7 April 2010
• 年：2010
• 卷：51
• 期：14
• 页码：1863-1866
• 全文大小：686 K

文摘

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.