Conclusions
The nitration of the methoxymethyl derivatives of secondary amides of general formula XN(AlK)CH2OCH3 by nitronium tetrafluoborate is accompanied either by cleavage of the N-CH2 bond to give alkylnitroamides or by cleavage of the O-CH2 bond to give methylenebisalkylamides or else it proceeds along both possible directions.
Literature cited
O. A. Luk'yanov, T. G. Mel'nikova, and V. A. Tartakovskii, Izv. Akad. Nauk SSSR, Ser. Khim.,1981, 2335.
C. A. Olah and J. M. Bollinger, J. Am. Chem. Soc.,89, 2993 (1967).
E. H. White, M. C. Chen, and L. A. Dolak, J. Org. Chem.,31, 3038 (1966).
O. A. Luk'yanov, V. P. Gorelik, V. A. Tartakovskii, and S. S. Novikov, Izv. Akad. Nauk SSSR, Ser. Khim.,1971, 1804.
R. C. Brain and A. H. Lamberton, J. Chem. Soc.,1949, 1633.
S. D. Ross, M. Finkelstein, and E. J. Rudd, J. Org. Chem.,37, 2387 (1972).
L. Goodman, J. Am. Chem. Soc.,75, 3019 (1953).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2610–2611, November, 1981.
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Luk'yanov, O.A., Mel'nikova, T.G., Kashirskaya, E.G. et al. Nitration of N-methoxymethyl-substituted secondary amides by nitronium tetrafluoborate. Russ Chem Bull 30, 2167–2168 (1981). https://doi.org/10.1007/BF01094650
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DOI: https://doi.org/10.1007/BF01094650