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First synthesis of nitro-substituted bicyclo[1.1.0]butane derivatives and new method for generation of tricyclo[4.1.0.02,7]hept-1(7)-ene

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Abstract

Successive treatment of 1-phenylsulfonyltricyclo[4.1.0.02,7]heptane with butyllithium and ethyl nitrate leads to the formation of 7-nitro-7′-phenylsulfonyl-1,1′-bi(tricyclo[4.1.0.02,7]heptane) through intermediate tricyclo[4.1.0.02,7]hept-1(7)-ene which is generated by 1,2-elimination of benzenesulfinic acid from the initial compound. Analogous treatment of 1-phenyltricyclo[4.1.0.02,7]heptane gives 1-nitro-7-phenyltricyclo[4.1.0.02,7]heptane.

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Authors and Affiliations

  1. Ogarev Mordovian State University, ul. Bol’shevistskaya 68, Saransk, 430000, Russia

    V. A. Vasin & S. G. Kostryukov

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

    R. N. Zolotarev & V. V. Razin

Authors
  1. V. A. Vasin
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  2. S. G. Kostryukov
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  3. R. N. Zolotarev
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  4. V. V. Razin
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Additional information

Original Russian Text © V.A. Vasin, S.G. Kostryukov, R.N. Zolotarev, V.V. Razin, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 3, pp. 363–366.

For preliminary communication, see [6].

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Vasin, V.A., Kostryukov, S.G., Zolotarev, R.N. et al. First synthesis of nitro-substituted bicyclo[1.1.0]butane derivatives and new method for generation of tricyclo[4.1.0.02,7]hept-1(7)-ene. Russ J Org Chem 43, 359–362 (2007). https://doi.org/10.1134/S1070428007030049

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  • DOI: https://doi.org/10.1134/S1070428007030049

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