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Nitronium esters in reactions of 1,3-addition

Communication 1. Reaction of O-methyl ester of phenylnitromethane with grignard reagents

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Conclusions

  1. 1.

    The reaction of the O-methyl ester of phenylnitromethane with various Grignard reagents of general formula RMgX occurs unambiguously, independent of the nature of R, and leads to the formation of secondary hydroxylamines of general formula C6H5CH(R)N(R)OH.

  2. 2.

    The reaction of the O-methyl ester of phenylnitromethane with RMgX occurs by the scheme of 1,3-addition, in which connection the formed intermediate product reacts at a faster rate with the RMgX than does the starting O-methyl ester of phenylnitromethane.

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Literature cited

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    V. A. Tartakovskii, I. E. Chlenov, S. S. Smagin, and S. S. Novikov, Izv. AN SSSR, Ser. Khim.,1964, 583.

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    M. Busch and L. Leefhelm, J. Prakt. Chem.,77, 20 (1908).

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    A. W. Johnson, J. Organ. Chem.,28, 252 (1963).

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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2522–2526, November, 1967.

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Ioffe, S.L., Shitov, O.P., Chlenov, I.E. et al. Nitronium esters in reactions of 1,3-addition. Russ Chem Bull 16, 2399–2402 (1967). https://doi.org/10.1007/BF00911852

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Keywords

  • Ester
  • Fast Rate
  • General Formula
  • Intermediate Product
  • Hydroxylamine