Research Article: (1R,2R)-N,N′-Diisobutyl-N,N′-dimethyl­cyclo­hexane-1,2-diamine

Date Published: May 01, 2009

Publisher: International Union of Crystallography

Author(s): Prisca K. Eckert, Viktoria H. Gessner, Carsten Strohmann.

http://doi.org/10.1107/S160053680901109X

Abstract

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.

Partial Text

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 ▶).

 

Source:

http://doi.org/10.1107/S160053680901109X

 

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