Synthesis and Ring Strain of a Benzoborirene‐N‐Heterocyclic Carbene Adduct. Issue 70 (16th November 2018)

• Record Type: Journal Article
• Authors: Hahn, Jennifer; Keck, Constanze; Maichle‐Mössmer, Cäcilia; von Grotthuss, Esther; Ruth, Paul Niklas; Paesch, Alexander; Stalke, Dietmar; Bettinger, Holger F.
• Is Part Of: Chemistry. Volume 24:Issue 70(2018)
• Page Start: 18634
• Page End: 18637
• Publication Date: 2018-11-16
• Subjects: boron -- fused ring systems -- heterocycles -- strained molecules -- ylides; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201804629
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The reduction of an N ‐heterocyclic carbene (1, 3‐diisopropyl‐4, 5‐dimethylimidazolin‐2‐ylidene, I i Pr Me 2 ) adduct of dichloro( ortho ‐bromophenyl)borane by tert ‐butyl lithium at low temperature yields the I i Pr Me 2 adductA of parent benzoborirene, a highly strained boron‐containing bicyclic compound.A is unstable at room temperature and dimerizes at low temperature to the bis‐I i Pr Me 2 adduct of 9, 10‐dihydro‐9, 10‐diboraanthracene, characterized by single‐crystal X‐ray crystallography. Abstract : Boron under strain : A benzannulated borirene molecule with coordinated N ‐heterocyclic carbene I i Pr Me 2 is synthetically accessible. The ring strain of the compound is high and facilitates facile dimerization.