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Photochemistry of trifluromethyl substituted 1-methylpyrazoles

✍ Scribed by James W. Pavlik; Theppawut Israsena Na Ayudhaya; Chennagiri R. Pandit; Supawan Tantayanon

Book ID: 102341934
Publisher: Journal of Heterocyclic Chemistry
Year: 2004
Tongue: English
Weight: 209 KB
Volume: 41
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570410110

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✦ Synopsis

Trifluoromethyl substitution on the pyrazole ring was found to enhance photoreactivity via the P 4 pathway which involves interchange of the N2-C3 ring atoms. Thus, 1-methyl-3-(trifluoromethyl)pyrazole (1) and 1methyl-5-(trifluoromethyl)pyrazole (3) transposed with a P 4 /P 6 or P 4 /P 6 +P 7 ratio of 2.1:1. 1-Methyl-4-(trifluoromethyl)pyrazole (2) transposed regiospecifically by the P 4 transposition pathway. Compounds 2 and 3 were also observed to undergo photocleavage to yield enaminonitrile and enaminoisocyanide products.

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