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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.

SUBMITTER: Xu S

PROVIDER: S-EPMC3241830 | biostudies-other | 2011 Dec

REPOSITORIES: biostudies-other

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A 1,3-dihydro-1,3-azaborine debuts.

Xu Senmiao S Zakharov Lev N LN Liu Shih-Yuan SY

Journal of the American Chemical Society 20111121 50

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 react ...[more]

PMID: 22091703

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