Halogenation of vinyl ketoximes. Synthesis of isoxazoles and preparation and silver ion??promoted reactions of 4??halo??2??isoxazolines

…, SE Mccrotty, SA Strong, DE Zimmer

Index: Hansen, John F.; Kim, Yong In; McCrotty, Stephen E.; Strong, Scott A.; Zimmer, Douglas E. Journal of Heterocyclic Chemistry, 1980 , vol. 17, p. 475 - 479

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Citation Number: 12

Abstract

Abstract Reaction of several α, β-unsaturated ketoximes with N-bromosuccinimide (NBS) gave isoxazoles, but yields were lower and the reaction less general than a similar transformation using iodine under basic conditions. With β, β-disubstituted oximes, 4-halo-5, 5-disubstituted-2-isoxazolines were obtained using NBS, iodine, or N-chlorosuccinimide. Treatment of the 4-bromoisoxazo-lines with silver acetate or silver nitrate caused either ...