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Reaction of 1-h- and 1,2-di-h-cyclopropene compounds and their trimethylsilyl derivatives with 1,3-cyclopentadiene

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

Conclusions

  1. 1.

    The adducts of 1,3-cyclopentadiene with the esters of 1-H-2-alkyl- and 1,2-di-H-cyclopropene-3-carboxylic acids were obtained under the conditions for the hydrolytic cleavage of the trimethylsilyl groups from the esters of i-alkyl-2-(trimethylsilyl)-or 1,2-bis(trimethylsilyl)cyclopropene-3-carboxylic acids at temperatures ranging from −40 to−5°, which when saponified gave the corresponding acids. In a similar manner, 2-n-butyl-3-acetyltricyclo[3.2.1.02,4]oct-6-ene was obtained from 1-n-butyl-2-(trimethylsilyl)-3-acetylcyclopropene and cyclopentadiene.

  2. 2.

    The activity of cyclopropene compounds in the diene synthesis reaction is determined both by the nature of the substituents attached to the multiple bond of the cyclopropene and by the steric accessibility of this bond.

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Literature cited

  1. K. B. Wiberg and W. J. Bartley, J. Am. Chem. Soc.,82, 6375 (1960).

    Google Scholar 

  2. R. M. Magid and T. C. Clarke, J. Org. Chem.,36, 1320 (1971).

    Google Scholar 

  3. T. H. Chan and D. Massuda, Tetrahedron Lett.,1975, 3383.

  4. I. E. Dolgii, G. P. Okonnishnikova, and O. M. Nefedov, Izv. Akad. Nauk SSSR, Ser. Khim.,1970, 197; O. M. Nefedov, I. E. Dolgii (Dolgij), G. P. Okonnishnikova (Okonnischnikova), and I. B. Shvedova (Schwedova), Angew. Chem.,84, 946 (1972).

  5. O. M. Nefedov, I. E. Dolgii, and É. A. Baidzhigitova, Izv. Akad. Nauk SSSR, Ser. Khim.,1975, 2842.

  6. K. Kimura, S. Hori, I. Minato, and Y. Odaira, Chem. Lett.,1973, 1209.

  7. C. S. Kraihanzel and M. L. Losee, J. Org. Chem.,27, 1983 (1968).

    Google Scholar 

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    I. E. Dolgii, G. P. Okonnishnikova, É. A. Baidzhigitova, A. Ya. Shteinshneider & O. M. Nefedov

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  1. I. E. Dolgii
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  2. G. P. Okonnishnikova
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  3. É. A. Baidzhigitova
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  4. A. Ya. Shteinshneider
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  5. O. M. Nefedov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2592–2596, November, 1977.

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Dolgii, I.E., Okonnishnikova, G.P., Baidzhigitova, É.A. et al. Reaction of 1-h- and 1,2-di-h-cyclopropene compounds and their trimethylsilyl derivatives with 1,3-cyclopentadiene. Russ Chem Bull 26, 2401–2404 (1977). https://doi.org/10.1007/BF00958739

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  • DOI: https://doi.org/10.1007/BF00958739

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