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

doi:10.1021/ol901984x

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

Org Lett. 2009 Oct 15;11(20):4684-7. doi: 10.1021/ol901984x.

Authors

Jing Kong¹, Debjani Roy, Dieter Lenoir, Xiangwen Zhang, Ji-jun Zou, Paul von Ragué Schleyer

Affiliation

¹ Key Laboratory for Green Chemical Technology of Ministry of Education, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China.

PMID: 19775103
DOI: 10.1021/ol901984x

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.