Date Published: May 01, 2009
Publisher: International Union of Crystallography
Author(s): Prisca K. Eckert, Viktoria H. Gessner, Carsten Strohmann.
The title compound, C16H34N2, is a chiral diamine with fixed R configuration at both stereogenic carbon centres of the cyclohexane backbone. Due to their different substituents, the two N atoms also become stereogenic. In the crystal structure, the configuration at one of the two nitrogen centres is fixed, with the free electron pair pointing inward and the isobutyl group in a trans position towards the cyclohexane backbone resulting in an R configuration. The isobutyl group at the second N atom, however, is disordered with 75% S configuration and 25% R configuration. In both cases, the isobutyl group is arranged in a trans position towards the cyclohexane backbone.
The synthesis of the title compound is described by Kizirian et al. (2003 ▶). For the crystal structure of the related molecule (1R,2R)-N,N′-dimethylcyclohexane-1,2-diamine, see Strohmann et al. (2008b ▶). Crystal structures of (1R,2R)-N,N′-tetramethylcyclohexane-1,2-diamine coordinated to lithium organyls are described by Strohmann & Gessner (2007a ▶) and Strohmann & Gessner (2008 ▶). Other related diamines coordinated to lithium organyls are specified by Strohmann & Gessner (2007b ▶) and Strohmann et al. (2008a ▶). The use of chiral nitrogen ligands to enhance the stereoselectivity of deprotonation or addition reactions is discussed by Kizirian (2008 ▶) and Stead et al. (2008 ▶).