期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 82, 期 12, 页码 6313-6326出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00904
关键词
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资金
- Japan Society for the Promotion of Science [15K14927]
- Grants-in-Aid for Scientific Research [16K08157, 15K14927, 16H00822] Funding Source: KAKEN
An experimental study of base-induced transformation reaction of 2-acyl-3-alkyl-2H-azirines to oxa-zoles indicated that a deprotonation-initiated mechanism is involved, in addition to nucleophilic addition to the imine functionality. Calculations suggested the participation of a ketenimine (ethenimine) intermediate generated by azirine ring opening of the carbanion intermediate formed by alpha-deprotonation of 2H-azirine. The ketenimine intermediate possessing methyl substituents at C(3) appears to be more stable than the tautomeric nitrile ylide which was proposed to be involved in photoinduced and pyrolysis reactions of 2-acyl-3-alkyl-2H-azirines to afford oxazoles. Thus, intermediacy of ketenimine is consistent with both experimental and computational results, at least under strongly basic reaction conditions.
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