Stereoselective and stereospecific reactions. III. Benzoylation, cyclization, and epimerization of diols.
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概要
- 論文の詳細を見る
The benzoylation of various classes of diols by means of diethyl azodicarboxylate (<B>1</B>) and triphenylphosphine (<B>2</B>) was carried out at room temperature. When primary–secondary diols were treated with an equimolar amount of benzoic acid (<B>3</B>) in the presence of 1.5 molar equivalents of <B>1</B> and <B>2</B>, reaction mainly Occurred at their primary hydroxyl functions. Secondary–secondary diols gave mono- and dibenzoylated products or cyclic ethers. The course of the reactions depends on the structure of diols used. Thus, intermolecular displacement giving benzoates is a favorable process for 1,3-butanediol, 2,4-pentanediol and <I>trans</I>-1,2-indanediol, while 2,5-hexanediol and <I>trans</I>-1,2-cyclohexanediol afford the cyclized products.
- 公益社団法人 日本化学会の論文
著者
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Kimura Junji
Department Of Chemistry And Biological Science College Of Science And Engineering Aoyama Gakuin Univ
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Mitsunobu Oyo
Department Of Chemistry College Of Science And Engineering Aoyama Gakuin University
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Yanagida Noboru
Department Of Agricultural Chemistry The University Of Tokyo:(present Office)biological Science Inst
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Yanagida Noboru
Department of Chemistry, College of Science and Engineering, Aoyama Gakuin University
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Iiizumi Ken-ichi
Department of Chemistry, College of Science and Engineering, Aoyama Gakuin University
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