Synthesis and crystal structure of 2-(anthracen-9-yl)-1-(tert-butyldimethylsilyl)-3,6-dihydro-1λ4,2λ4-azaborinine

Author:

Gliese Philipp J.ORCID,Appiarius YannikORCID,Scheele TarekORCID,Lork Enno,Neudecker Tim,Staubitz Anne

Abstract

The title compound, C24H30BNSi (I), is an asymmetric 1,2,3,6-tetrahydro-1,2-azaborinine consisting of a BN-substituted cyclohexadiene analog with a B-anthracenyl substituent. A ring-closing metathesis with subsequent substitution of the obtained BCl 1,2-azaborinine using anthracenyl lithium yielded the title compound I. The asymmetric unit (Z = 8) belongs to the orthorhombic space group Pbca and shows an elongated N—C bond compared to previously reported BN-1,4-cyclohexadiene [Abbey et al. (2008) J. Am. Chem. Soc. 130, 7250–7252]. The primarily contributing surface interactions are H...H and C...H/H...C (as elucidated by Hirshfeld surface analysis) which are dominated by van der Waals forces. Moreover, the non-aromatic BN heterocycle and the protecting group exhibit intra- and intermolecular C—H...π interactions, respectively, with the anthracenyl substituent.

Funder

Deutsche Forschungsgemeinschaft

Publisher

International Union of Crystallography (IUCr)

Subject

Condensed Matter Physics,General Materials Science,General Chemistry

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