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American Chemical Society, Organic Letters, 20(11), p. 4684-4687, 2009

DOI: 10.1021/ol901984x

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2-Norbornyl Ion-Pair Leakage in Electrophilic Addition of HCl to Nortricyclene and Norbornene

Journal article published in 2009 by Jing Kong, Paul von Ragué Schleyer, Debjani Roy, Dieter Lenoir, Xiangwen Zhang, Ji-Jun Zou ORCID, Paul von Ragué Schleyer
This paper is available in a repository.
This paper is available in a repository.

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Abstract

Ion pair "leakage" pathways, located computationally by means of multidimensional potential energy surface scans, rationalize the unsymmetrical D-label scrambling observed experimentally in the DCl addition products of nortricyclene and norbornene. "Classical" addition transition structures can interconvert ("leak") to symmetrical nonclassical 2-norbornyl ion pair species, either TS's or a minimum, before products form.