New Findings in Photochemistry of <i>p</i>-Nitrophenyl Azide in the Presence of an Amine: Generation and Trapping of Enamines

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  • Shigeru Murata
    Department of Basic Science, Graduate School of Arts and Sciences, The University of TokyoMeguro-ku, Tokyo
  • Yoko Mori
    Chemistry Department for Materials, Faculty of Engineering, Mie UniversityTsu, Mie
  • Youji Satoh
    Chemistry Department for Materials, Faculty of Engineering, Mie UniversityTsu, Mie
  • Ryuichi Yoshidome
    Chemistry Department for Materials, Faculty of Engineering, Mie UniversityTsu, Mie
  • Hideo Tomioka
    Chemistry Department for Materials, Faculty of Engineering, Mie UniversityTsu, Mie

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<jats:title>Abstract</jats:title> <jats:p>4,5-Dihydro-5-diethylamino-1-(p-nitrophenyl)-1,2,3-triazole (3) was obtained in the photolysis of p-nitrophenyl azide (1) in triethylamine (TEA), for which the structure was determined by X-ray crystallographic analysis. The formation of the triazoline 3 is reasonably explained in terms of trapping of N,N-diethylvinylamine (5) generated in situ with the starting azide 1. The reaction sequence involving a single electron transfer from TEA to the electronically excited azide is proposed for the formation of the enamine 5.</jats:p>

収録刊行物

  • Chemistry Letters

    Chemistry Letters 28 (7), 597-598, 1999-07-01

    Oxford University Press (OUP)

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