Bent structure and dynamic stereochemistry of chiral acridinium cations

Benoît Laleu; Christelle Herse; Bo W Laursen; Gérald Bernardinelli; Jérôme Lacour

doi:10.1021/jo0345998

Bent structure and dynamic stereochemistry of chiral acridinium cations

J Org Chem. 2003 Aug 8;68(16):6304-8. doi: 10.1021/jo0345998.

Authors

Benoît Laleu¹, Christelle Herse, Bo W Laursen, Gérald Bernardinelli, Jérôme Lacour

Affiliation

¹ Département de Chimie Organique, Université de Genève, quai Ernest-Ansermet 30, CH-1211 Genève 4, Switzerland.

PMID: 12895064
DOI: 10.1021/jo0345998

Abstract

Chiral acridinium cations, easily prepared by reaction of enantiopure primary amines and tris(2,6-dimethoxy)trityl cation, display restricted rotations around the C(sp(3))-N(sp(2)) bond. A bending of the aromatic backbone and "out-of-plane" displacements of C(9) and N(10) atoms are enforced if bulky amines are introduced.