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The Cyclopropylcarbinyl Cation

  • Chapter
The Nonclassical Ion Problem

Abstract

The fascinating behavior of cyclopropylcarbinyl derivatives in solvolytic processes and other carbonium ion transformations1 was explored in detail by J. D. Roberts and his coworkers.2 The exceptionally fast rate of solvolysis and the facile interconversions of cyclopropylcarbinyl, cyclobutyl, and allylcarbinyl derivatives led to the proposal that σ-bridged intermediates were involved. Indeed, the first use of the term “nonclassical ion,” appears to have been Roberts’ proposed tricyclobutonium structure 2 for the cyclopropylcarbinyl cation 1 3 (1).

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Authors and Affiliations

  1. Purdue University, West Lafayatte, Indiana, USA

    Herbert C. Brown

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  1. Herbert C. Brown
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© 1977 Plenum Press, New York

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Brown, H.C. (1977). The Cyclopropylcarbinyl Cation. In: The Nonclassical Ion Problem. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-4118-5_5

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  • DOI: https://doi.org/10.1007/978-1-4613-4118-5_5

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-4120-8

  • Online ISBN: 978-1-4613-4118-5

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