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σ-Complexes of transition metals in organic synthesis. 9. Reactions of allyl organomanganese compounds with γ-bromine derivatives of esters of α, Β-unsaturated carboxylic acids

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

Abstract

The allyl Mn(II) organic compounds R1CH=C(R2)CH2MnCl (R1=H, Me; R2=H, Me, Bu), obtained in situ from Grignard reagents and Li2MnCl4, react with esters of 4-bromocrotonic, (2-bromobutylidene)-, (4-bromo-2-butenylidene)-, (2-bromoisobutylidene) malonic, and (2-bromoheptylidene)cyanoacetic acids in THF at −78 to +20‡C to give derivatives of substituted cyclopropanecarboxylic or cyclopropane-1, 1-dicarboxylic acids. These derivatives contain a fragment of the allyl type. When ethers of 2-(bromomethyl)acrylic, 4-bromo-2-methyl-, and 4-bromo-3-methyl-2-butenoic acids are used, cross-combination products result.

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Literature cited

  1. A. N. Kasatkin, O. Yu. Tsypyshev, T. Yu. Romanova, and G. A. Tolstikov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1154 (1990).

    Google Scholar 

  2. P. Prempree, S. Radviroongit, and Y. Thebtaranonth, J. Org. Chem.,48, 3553 (1983).

    Google Scholar 

  3. M. Yamaguchi, M. Tsukamoto, and I. Hirao, Tetrahedron Lett.,26, 1723 (1985).

    Google Scholar 

  4. M. Joucla, M. E. Goumzili, and B. Fouchet, Tetrahedron Lett.,27, 1677 (1986).

    Google Scholar 

  5. E. Ghera and Y. Ben-David, Tetrahedron Lett., 4603 (1979).

  6. R. D. Little and J. W. Dawson, Tetrahedron Lett.,21, 2609 (1980).

    Google Scholar 

  7. R. D. Little and J. R. Dawson, J. Am. Chem. Soc.,100, 4607 (1978).

    Google Scholar 

  8. R. S. Ratney and J. English, J. Org. Chem.,25, 2213 (1960).

    Google Scholar 

  9. G. H. Posner, in: Organic Reactions, W. G. Dauben (ed.), Vol. 19, Wiley, New York (1972), p. 1.

    Google Scholar 

  10. J. F. Normant and G. Cahiez, in: Modern Synthetic Methods, R. Scheffold (ed.), Vol. 3, Wiley, New York (1983), p. 173.

    Google Scholar 

  11. A. N. Kasatkin, O. Yu. Tsypyshev, T. Yu. Romanova, and G. A. Tolstikov, Metalloorg. Khim.,2, No. 4, 830 (1989).

    Google Scholar 

  12. A. N. Kasatkin, O. Yu. Tsypyshev, T. Yu. Romanova, and G. A. Tolstikov, Metalloorg. Khim.,2, No. 4, 837 (1989).

    Google Scholar 

  13. N. C. Rol and A. D. H. Claque, Org. Magn. Reson.,16, 187 (1981).

    Google Scholar 

  14. S. Tsuboi, K. Muranaka, T. Sakai, and A. Takeda, J. Org. Chem.,51, 4944 (1986).

    Google Scholar 

  15. L. M. Khalilov, A. A. Famykhov, V. S. Sulmanova, et al., Khim. Prir. Soedin., No. 2, 266 (1989).

    Google Scholar 

  16. R. D. Allan and B. Twitchin, Aust. J. Chem.,31, 2283 (1978).

    Google Scholar 

  17. L. Villieras and M. Rambaud, Synthesis, 924 (1982).

  18. A. N. Kasatkin, R. Kh. Biktimirov, G. A. Tolstikov, and L. M. Khalilov, Zh. Org. Khim.,26, No. 6, 1191 (1990).

    Google Scholar 

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For previous communication, see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 656–663, March, 1991.

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Kasatkin, A.N., Tsypyshev, O.Y., Romanova, T.Y. et al. σ-Complexes of transition metals in organic synthesis. 9. Reactions of allyl organomanganese compounds with γ-bromine derivatives of esters of α, Β-unsaturated carboxylic acids. Russ Chem Bull 40, 573–580 (1991). https://doi.org/10.1007/BF00957998

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  • DOI: https://doi.org/10.1007/BF00957998

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