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Synthesis of 7-sulfonyl-substituted norpinan-6-ones and -thiones from 1-bromotricyclo[4.1.0.02,7]heptane

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Abstract

1-Bromotricyclo[4.1.0.02,7]heptane reacted with benzene- and methanesulfonyl thiocyanates in benzene at 20°C via anti addition to the central C1–C7 bicyclobutane bond with formation of 6-endo-bromo-6-exo-thiocyanato-7-syn-(R-sulfonyl)bicyclo[3.1.1]heptanes. Treatment of the benzenesulfonyl thiocyanate adduct with potassium tert-butoxide in THF at 20°C gave 7-endo-(benzenesulfonyl)norpinan-6-one, whereas the reaction with 1,8-diazabicyclo[5.4.0]undec-7-ene in methylene chloride afforded 7-exo-(benzenesulfonyl)-norpinane-6-thione which was converted into 7-exo-(benzenesulfonyl)norpinan-6-one by alkaline hydrolysis.

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Authors and Affiliations

  1. Ogarev Mordovian State University, ul. Bol’shevistskaya 68, Saransk, 430005, Russia

    V. A. Vasin, D. Yu. Korovin & P. S. Petrov

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

    V. V. Razin

  3. Lobachevskii State University of Nizhny Novgorod, pr. Gagarina 23, Nizhny Novgorod, 603950, Russia

    N. V. Somov

Authors
  1. V. A. Vasin
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  2. D. Yu. Korovin
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  3. P. S. Petrov
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  4. V. V. Razin
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  5. N. V. Somov
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Correspondence to V. A. Vasin.

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Original Russian Text © V.A. Vasin, D.Yu. Korovin, P.S. Petrov, V.V. Razin, N.V. Somov, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 12, pp. 1732–1736.

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Vasin, V.A., Korovin, D.Y., Petrov, P.S. et al. Synthesis of 7-sulfonyl-substituted norpinan-6-ones and -thiones from 1-bromotricyclo[4.1.0.02,7]heptane. Russ J Org Chem 51, 1697–1702 (2015). https://doi.org/10.1134/S1070428015120052

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  • DOI: https://doi.org/10.1134/S1070428015120052

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