title: Protecting group-free synthesis of 1,2-azaborines: a simple approach to the construction of BN-benzenoids.
abstract: The protecting group-free synthesis of a versatile 1,2-azaborine synthon 5 is described. Previously inaccessible 1,2-azaborine derivatives, including the BN isostere of phenyl phenylacetate and BN1 triphenylmethane were prepared from 5 and characterized. The structural investigation of BN phenyl phenylacetate revealed the presence of a unique NH-carbonyl hydrogen bond that is not present in the corresponding carbonaceous analogue. The methyne CH in BN triphenylmethane was found to be less acidic than the corresponding proton in triphenylmethane. The gram-quantity synthesis of the parent 1,2-azaborine 4 was demonstrated, which enabled the characterization of its boiling point, density, refractive index, and its polarity on the ET(30) scale.
authors.affiliation: Department of Chemistry and Biochemistry, University of Oregon, Eugene, Oregon 97403, USA.
authors.forename: Eric R
authors.initials: ER
authors.lastname: Abbey
authors.forename: Ashley N
authors.initials: AN
authors.lastname: Lamm
authors.forename: Andrew W
authors.initials: AW
authors.lastname: Baggett
authors.forename: Lev N
authors.initials: LN
authors.lastname: Zakharov
authors.forename: Shih-Yuan
authors.initials: SY
authors.lastname: Liu
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D001895:Boron / Q000737:chemistry*; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*
chemical_list: C556261:1,2-azaborine; D001555:Benzene Derivatives; D001896:Boron Compounds; D009584:Nitrogen; D001895:Boron
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