Benzenesulfonylcarbonitrile Oxide. 4. Substitution Reactions of 3-(Phenylsulfonyl)isoxazolines

Abstract

3-(Phenysulfonyl)isoxazolines, readily obtained from alkenes by cycloaddition with benzenesulfonylcarbonitrile oxide, undergo a variety of substitution reactions. Alkyl, aryl, and acetylenic lithium reagents, cyanide, lithium or sodium alkoxides, and sodium borohydride are all useful nucleophiles. Tandem alkylations are possible with alkyllithium reagents when excess base and alkyl iodide are used. Excess base can also be used to cleave the isoxazoline ring of the initial substitution products. 3-(2-Propenyloxy)isoxazolines will undergo an aza-Claisen rearrangement on heating. © 1983, American Chemical Society. All rights reserved.