Synthesis and crystal structure of 2-(anthracen-9-yl)-1-(tert-butyldimethylsilyl)-3,6-dihydro-1 λ 4,2 λ 4-azaborinine

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.

Source: Acta Crystallographica Section E - October 10, 2023 Category: Chemistry Authors: Gliese, P.J. Appiarius, Y. Scheele, T. Lork, E. Neudecker, T. Staubitz, A. Tags: crystal structure 1,2-azaborinine boron – nitrogen bond nitrogen heterocycle ring-closing metathesis BN cyclohexene research communications Source Type: research