title: A 1,3-dihydro-1,3-azaborine debuts.
abstract: We present the first synthesis and characterization of a 1,3-dihydro-1,3-azaborine, a long-sought BN isostere of benzene. 1,3-Dihydro-1,3-azaborine is a stable structural motif with considerable aromatic character as evidenced by structural analysis and its reaction chemistry. Single crystal X-ray analysis indicates bonding consistent with significant electron delocalization. 1,3-Dihydro-1,3-azaborines also undergo nucleophilic substitutions at boron and electrophilic aromatic substitution reactions. In view of the versatility and impact of aromatic compounds in the biomedical field and in materials science, the present study further expands the available chemical space of arenes via BN/CC isosterism.
authors.affiliation: Department of Chemistry, University of Oregon, Eugene, Oregon 97403-1253, USA.
authors.forename: Senmiao
authors.initials: S
authors.lastname: Xu
authors.forename: Lev N
authors.initials: LN
authors.lastname: Zakharov
authors.forename: Shih-Yuan
authors.initials: SY
authors.lastname: Liu
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006571:Heterocyclic Compounds / Q000737:chemistry
chemical_list: D001372:Aza Compounds; D001896:Boron Compounds; D006571:Heterocyclic Compounds
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