The Reaction of Alcohols with Hexamethylphosphoric Triamide

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概要

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• The thermal treatment of 4-homoadamantanol and bicyclo[3.3.1]nonanols with hexamethylphosphoric triamide (HMPT) gave the corresponding olefins in moderate yields. The application of this dehydration method to a system in which olefin formation was regarded as difficult or impossible stereochemically led to various types of reactions, <I>i.e.</I>, reduction, substitution, and phosphorodiamidation. Upon being heated in HMPT, 2-adamantanol afforded 2-adamantyl tetramethylphosphorodiamidate, whereas 1-adamantanol was transformed into adamantane <I>via</I> 1-adamantyl tetramethylphosphorodiamidate. In the case of allylic or benzylic alcohols, dimethylamino-substituted compounds were obtained. The reduction of the amount of HMPT promoted the formation of an ether, while dibenzhydryl ether was produced exclusively from benzhydrol. The mechanism of these reaction is discussed.

• 公益社団法人 日本化学会の論文

著者

• Kawanisi Mituyosi

  Department of Industrial Chemistry, Faculty of Engineering, Kyoto University

• Yamaguchi Ryohei

  Department of Applied Chemistry, Faculty of Engineering, Yokohama National University

• Kawanisi Mituyosi

  Department of Industrial Chemistry, Faculty of Engineering Kyoto University

• Arimatsu Seiji

  Department of Industrial Chemistry, Faculty of Engineering, Kyoto University

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