The Journal of Organic Chemistry

Sulfonylisoxazolines: reliable intermediates for the preparation of. beta.-hydroxy nitriles

PA Wade, JF Bereznak

Index: Wade, Peter A.; Bereznak, James F. Journal of Organic Chemistry, 1987 , vol. 52, # 14 p. 2973 - 2977

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Citation Number: 38

Abstract

Repetition of the reaction of sulfonylisoxazoline 8a with 2% Na-HgO in the presence of aqueous phosphate buffer led to formation of a mixture of P-hydroxy nitrile 16, 5 benzyl alcohol, and phenylacetonitrile. One problem encountered here was the destruction of the sodium amalgam by the buffer, necessitating a very large excess and periodic replenishment. Another problem was the critical pH dependence of the results: at a pH> ...

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