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Reactivity of compounds containing the ferrocenylmethyl group

Communication 7. Rearrangement of benzyl(ferrocenylmethyl)dimethyl ammonium chloride under the action of nucleophilic reagents

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    A study was made of the rearrangement of benzyl(ferrocenylmethyl)dimethylammonium chloride under the action of nucleophilic reagents (butyllithium, potassamide, and benzylmagnesium chloride), and it was shown that a ferrocene nucleus stabilizes an adjacent carbanionic center less powerfully than a benzene nucleus does.

  2. 2.

    A new type of ylid isomerization was discovered: it occurs when butyllithium acts on benzyl(ferrocenylrnethyl) dimethylammonium chloride.

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Literature cited

  1. É. G. Perevalova and Yu. A. Ustynyuk, Izv. AN SSSR, Otd, khim. n 1963, 1036.

  2. É. G. Perevalova, Yu. A. Ustynyuk, and A. N. Nesmeyanov, Izv. AN SSSR. Otd. khim. n. 1963, 1046.

  3. É. G. Perevalova and Yu. A. Ustynyuk, Izv. AN SSSR. Otd. khim. n. 1963, 1776.

  4. A. N. Nesmeyanov, É. G. Perevlaova, Yu. A. Ustynyuk, and L. A. Ustynyuk, Izv. AN SSSR. Ser. khim. 1963, 1972.

  5. A. N. Nesmeyanov, É. G. Perevalova, and Yu. A. Ustynyuk, Izv. AN SSSR. Ser. khim. 1963, 1977.

  6. T. Thomson and T. S. Stevens, J. Chem. Soc. 1932, 55.

  7. G. Wittig, H. Mangold, and G. Felletschin, Liebigs Ann. Chem.560, 116 (1948); G. M. Bennett and A. W. Chapman, Ann. Repts. on Progress Chem. (Chem. Soc. London),27, 123 (1930).

    Google Scholar 

  8. W. Q. Beard and C. R. Hauser, J. Organ. Chem.26, 371 (1961).

    Google Scholar 

  9. G. Wittig and M. Reiber, Liebigs Ann. Chem.562, 177 (1949); S. W. Kantor and C. R. Hauser, J. Amer. Chem. Soc. 73, 4122 (1951).

    Google Scholar 

  10. H. Hellman and D. Eberle, Liebigs Ann. Chem.,662, 188, (1963).

    Google Scholar 

  11. A. N. Nesmeyanov, É. G. Perevalova, and L. S. Shilovtseva, Izv. AN SSSR. Otd. khim. n. 1961,1982.

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Authors and Affiliations

  1. Institute of Heteroorganic Compounds, Academy of Sciences, USSR

    Yu. A. Ustynyuk & É. G. Perevalova

  2. M. V. Lomonosov Moscow State University, USSR

    Yu. A. Ustynyuk & É. G. Perevalova

Authors
  1. Yu. A. Ustynyuk
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  2. É. G. Perevalova
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The authors express their great indebtedness to A. N. Nesmeyanov for his interest in the work and valuable service.

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Ustynyuk, Y.A., Perevalova, É.G. Reactivity of compounds containing the ferrocenylmethyl group. Russ Chem Bull 13, 52–58 (1964). https://doi.org/10.1007/BF01179566

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  • DOI: https://doi.org/10.1007/BF01179566

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