The Journal of Organic Chemistry

Alkyl nitrate nitration of active methylene compounds. VI. Nitration of esters in liquid ammonia

H Feuer, RP Monter

Index: Feuer,H.; Monter,R.P. Journal of Organic Chemistry, 1969 , vol. 34, # 4 p. 991 - 995

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Citation Number: 9

Abstract

The nitration of aliphatic and phenyl acetate esters with alkyl nitrates in the presence of potassium amide in liquid ammonia gives not only a-nitro esters 1 but also nitroalkanes 2 and dialkyl carbonates 3. In addition to these compounds, another a-nitro ester 4 forms when the alkoxy portion of the ester and alkyl nitrate are not the same. Compounds 2 and 3 arise from a fragmentation reaction and compound 4 from a transesterification reaction, ...

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