Acid-catalyzed nitronate cycloaddition reactions. Useful syntheses and simple transformations of 3-acyl-and 3-alkenylisoxazolines

PA Wade, NV Amin, HK Yen, DT Price…

Index: Wade, Peter A.; Amin, Nayan V.; Yen, Hwa-Kwo; Price, David T.; Huhn, George F. Journal of Organic Chemistry, 1984 , vol. 49, # 24 p. 4595 - 4601

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Citation Number: 45

Abstract

Nitronic esters derived from primary nitro ketones, ethyl nitroacetate, and (phenylsulfony1) nitromethane react with dipolarophiles in the presence of nonaqueous protic and Lewis acids to give nitrile oxide cycloadducts. a-Nitro ketones, ethyl nitroacetate, and (phenylsulfony1) nitromethane give nitrile oxide cycloadducts in the presence of p- toluenesulfonic acid, although conditions are necessarily more vigorous. The anions of ...