The acid catalyzed decomposition of diazo compounds. I. Synthesis of oxazoles in the BF3 catalyzed reaction of diazo carbonyl compounds with nitriles.
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概要
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The BF<SUB>3</SUB>-catalyzed decomposition of diazo carbonyl compounds in nitriles have afforded the corresponding oxazoles in high yields. This method is applicable to diazo carbonyl compounds such as <I>m</I>- and <I>p</I>-substituted diazoacetophenones, ethyl diazoacetate, 1,2-diphenyl-2-diazoethanone, dibenzoyldiazomethane, and dimethyl diazomalonate. Bis(diazo ketone)s such as terminal bis(diazoacetylated) alkanes (III<SUB>1−4</SUB>: <I>n</I>=6, 8, 10, 12) and <I>m</I>-and <I>p</I>-bis(diazoacetyl)benzenes also gave the corresponding bisoxazoles in a similar reaction. The reaction has been interpreted in terms of a stepwise mechanism <I>via</I> betaine intermediates initiated by the attack of BF<SUB>3</SUB> on the carbonyl oxygen of diazo carbonyl compounds. The emission spectra of oxazoles are described.
- 公益社団法人 日本化学会の論文
著者
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Ibata Toshikazu
Institute Of Chemistry College Of General Education Osaka University
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Sato Ryohei
Institute of Chemistry, College of General Education, Osaka University
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