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Stereoselectivity of halomethoxylation of 1-phenyltricyclo-[4.1.0.02,7]heptane and methyl 7-phenyltricyclo[4.1.0.02,7]-heptane-1-carboxylate

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Abstract

The stereoselectivity of halomethoxylation of 1-phenyltricyclo[4.1.0.02,7]heptane and methyl 7-phenyltricyclo[4.1.0.02,7]heptane-1-carboxylate at the central bicyclobutane C1-C7 bond by the action of N-chloro-, N-bromo-, and N-iodosuccinimides in methanol depends on the halogen nature. Conjugate chlorination and bromination are characterized by pronounced anti-stereoselectivity; the contribution of syn-addition slightly increases in going from the monosubstituted tricycloheptane substrate to disubstituted. Iodomethoxylation of the latter is clearly syn-stereoselective.

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Authors and Affiliations

  1. St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia

    V. V. Razin, Yu. A. Makarychev & R. N. Zolotarev

  2. Ogarev Mordovian State University, Cheboksary, Russia

    V. A. Vasin

  3. Institut für Organische Chemie, Universität Leipzig, Johannisallee 29, D-04103, Leipzig, Germany

    L. Hennig & J. Baldamus

Authors
  1. V. V. Razin
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  2. Yu. A. Makarychev
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  3. R. N. Zolotarev
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  4. V. A. Vasin
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  5. L. Hennig
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  6. J. Baldamus
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Additional information

Original Russian Text © V.V. Razin, Yu.A. Makarychev, R.N. Zolotarev, V.A. Vasin, L. Hennig, J. Baldamus, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 6, pp. 822–829.

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Razin, V.V., Makarychev, Y.A., Zolotarev, R.N. et al. Stereoselectivity of halomethoxylation of 1-phenyltricyclo-[4.1.0.02,7]heptane and methyl 7-phenyltricyclo[4.1.0.02,7]-heptane-1-carboxylate. Russ J Org Chem 43, 817–824 (2007). https://doi.org/10.1134/S1070428007060048

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  • DOI: https://doi.org/10.1134/S1070428007060048

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