Phototransposition chemistry of 1-phenylpyrazole. Experimental and computational studies

Autor:	Douglas S. Burns, James W. Pavlik, Robert E. Connors, Edyth M. Kurzweil
Rok vydání:	1993
Předmět:	Azirine chemistry.chemical_compound Reaction mechanism Colloid and Surface Chemistry chemistry Computational chemistry Fluorescence spectrometry General Chemistry Biochemistry Catalysis Bond cleavage Excitation
Zdroj:	Journal of the American Chemical Society. 115:7645-7652
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja00070a008
Popis:	Photophysical and photochemical properties of 1-phenylpyrazole and 3-,4-, and 5-methyl-1-phenylpyrazoles have been investigated. INDO/S calculations agree with experimental measurements which show that the S 1 and T 1 states of these compounds are π,π * in character. Upon S 0 →S 1 (π,π * ) excitation, these 1-phenylpyrazoles undergo phototransposition via a P 4 permutation pathway. This process is consistent with a mechanism involving initial N-N bond cleavage followed by a 1,2-shift and cyclization to form the 1-phenylimidazole product. The 1,2-shift may occur via an undetected azirine intermediate
Databáze:	OpenAIRE
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