2-Norbornyl ion-pair leakage in electrophilic addition of HCl to nortricyclene and norbornene.

Jing Kong, Debjani Roy, Dieter Lenoir, Xiangwen Zhang, Ji-jun Zou, Paul von Ragué Schleyer
Author Information
  1. Jing Kong: Key Laboratory for Green Chemical Technology of Ministry of Education, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China.

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.

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