The Journal of Organic Chemistry

O-Trimethylsilyl hydroxamoyl chlorides as nitrile oxide precursors

RF Cunico, L Bedell

Index: Cunico, Robert F.; Bedell, Louis Journal of Organic Chemistry, 1983 , vol. 48, # 16 p. 2780 - 2782

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Citation Number: 25

Abstract

Treatment of 3a, b with potassium fluoride in acetonitrile containing various olefins resulted in the formation of A2-isoxazolines 4a, b (Table I). The yields of cycloadduds thus obtained, even on the small scale employed, compare favorably with those reported using other methodologies. 2 Preliminary experiments have also indicated that 3a (but not 3b) thermolyzes in refluxing toluene to afford nitrile oxide. Thus a 57?% yield of 3-methyl-5-n- ...