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Types, Symbolism of Representation of Steric Structure, and Conformations of Ion Pairs. Stereochemical Version of the Generalized Rule of Elimination

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Abstract

Analysis of published data from the standpoint of the generalized rule of elimination demonstrated that in addition to contact and solvent-separated ion pairs, in elimination a species of a third type is generated, called spatially separated ion pair. This is an intermediate formed on the pathway of transformation of a contact ion pair to a solvent-separated one. Each of these ion pairs preserves its initial configuration of the bond C-nucleofuge starting from its origination to transformation into an elimination product, demonstrating discrete and inherent regio- and stereoselectivity: a contact ion pair shows nucleophilically controlled syn reactivity, and spatially- and solvent-separated ion pairs, electrophilically controlled syn and anti reactivity, respectively. The generalized rule of elimination allows almost faultless prediction of regio- and stereo- selectivity, being applicable to interpretation of even those published data which appear surprising or abnormal from the standpoint of the modern theoretical views.

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Authors and Affiliations

  1. Institute of Organic Chenistry, National Academy of Sciences of Armenia, Yerevan, Armenia

    A. A. Gevorkyan, A. S. Arakelyan, K. A. Petrosyan & A. Kh. Margaryan

  2. Yerevan State University, Yerevan, Armenia

    A. A. Gevorkyan, A. S. Arakelyan, K. A. Petrosyan & A. Kh. Margaryan

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  1. A. A. Gevorkyan
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  2. A. S. Arakelyan
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  3. K. A. Petrosyan
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  4. A. Kh. Margaryan
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Gevorkyan, A.A., Arakelyan, A.S., Petrosyan, K.A. et al. Types, Symbolism of Representation of Steric Structure, and Conformations of Ion Pairs. Stereochemical Version of the Generalized Rule of Elimination. Russian Journal of General Chemistry 71, 729–735 (2001). https://doi.org/10.1023/A:1012305301604

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