On the base catalysed ring opening of 3-unsubstituted isoxazoles. Derivatives of 4- and 5-phenylisoxazole
- 1 January 1977
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 9,p. 1121-1124
- https://doi.org/10.1039/p29770001121
Abstract
The kinetics of the base-induced decomposition of 4- and 5-phenylisoxazole and their p-bromo- and p-nitrophenyl derivatives, and 3-deuterio-5-phenylisoxazole, to the corresponding cyanoenolate anions have been studied. The mechanism of reaction has been established as a one-stage concerted abstraction of the proton in position 3 and scission of the N–O bond. 4-Phenylisoxazole, previously synthesized by laborious methods, has been prepared by a simpler procedure.Keywords
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