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Stereochemistry of conjugate halogenation of 1-phenyltricyclo[4.1.0.02,7]heptane

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Abstract

1-Phenyltricyclo[4.1.0.02,7]heptane reacts with N-bromo- and N-chlorosuccinimides in the presence of external nucleophiles providing products of a conjugate (electrophilic with respect to halogen) addition across the central bond C1-C7 of the bicyclo[3.1. 1]heptane structure with a pronounces endo, anti-stereoselectivity. In similar reactions with N-iodosuccinimide the products obtained originated mainly from endo, syn-addition across the C1-C7 bond. The reasons for differences in the selectivity of the conjugate halogenation are discussed applying the data of the quantum-chemical calculation in the basis MP2/STO 3G of the electronic and spatial structure of the reaction intermediates, norpinanyl cations of benzyl type.

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Authors and Affiliations

  1. Ogarev Mordovia State University, 430000, Saransk, Russia

    V. A. Vasin & A. V. Semenov

  2. Saint-Petersburg State University, 198904, St. Petersburg, Russia

    V. V. Razin

Authors
  1. V. A. Vasin
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  2. A. V. Semenov
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  3. V. V. Razin
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Translated from Zhurnal Organicheskoi Khimii, Vol. 40, No. 11, 2004, pp. 1647–1655.

Original Russian Text Copyright © 2004 by Vasin, Semenov, Razin.

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Vasin, V.A., Semenov, A.V. & Razin, V.V. Stereochemistry of conjugate halogenation of 1-phenyltricyclo[4.1.0.02,7]heptane. Russ J Org Chem 40, 1599–1607 (2004). https://doi.org/10.1007/s11178-005-0066-5

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  • DOI: https://doi.org/10.1007/s11178-005-0066-5

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