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Reaction of 2‐(Polyfluoroacyl)cycloalkanones with Hydroxylamine
Author(s) -
Sevenard Dmitri V.,
Khomutov Oleg G.,
Pashkevich Kazimir I.,
Lork Enno,
Röschenthaler GerdVolker
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200207)85:7<1960::aid-hlca1960>3.0.co;2-6
Subject(s) - chemistry , hydroxylamine , cycloalkane , yield (engineering) , ring (chemistry) , crystal structure , group (periodic table) , medicinal chemistry , stereochemistry , organic chemistry , catalysis , metallurgy , materials science
The 2‐acylcycloalkanones 1a – g and 3a – c , possessing a polyfluoroalkyl group, react with hydroxylamine regio‐ and stereoselectively to yield 4,5‐dihydroisoxazol‐5‐ols 2a – g and 4a – c , respectively, i.e. , products of N‐addition to the oxo group at the cycloalkane ring ( Schemes 1 and 2 ). The products 2 and 4 can be dehydrated under drastic conditions only ( Schemes 3 and 4 ). The structure of one of the 4,5‐dihydroisoxazol‐5‐ols was confirmed by X‐ray crystal‐structure analysis.