Tetrahedron

The N-ethylbenzisoxazolium cation—I: Preparation and reactions with nucleophilic species

DS Kemp, RB Woodward

文献索引：Kemp,D.S.; Woodward,R.B. Tetrahedron, 1965 , vol. 21, p. 3019 - 3035

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被引用次数: 54

摘要

The preparation and properties of the N-ethylbenzisoxazolium cation are described. The cation is shown to react rapidly in aqueous solution with a wide variety of nucleophiles, yielding o-hydroxy-N-ethylbenzimido derivatives. With carboxylate, cyanate, or thiocyanate anions, or with thiourea, internal rearrangements occur, converting the imido adducts to O- substituted products. The reactions of N-alkylated benzisoxazoles generate a broad ...