Literature DB >> 18479099

Crystal clear structural evidence for electron delocalization in 1,2-dihydro-1,2-azaborines.

Eric R Abbey1, Lev N Zakharov, Shih-Yuan Liu.   

Abstract

The first examples of "pre-aromatic" 1,2-dihydro-1,2-azaborine heterocycles have been structurally characterized, enabling the direct comparison of delocalized bonds of 1,2-dihydro-1,2-azaborines to their corresponding formal double and single bonds in nonaromatic systems. The crystallographic data provide an unprecedented look into the structural changes that occur in six-membered BN-heterocycles on their road to aromaticity, and they establish with little ambiguity that 1,2-dihydro-1,2-azaborines possess delocalized structures consistent with aromaticity.

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Year:  2008        PMID： 18479099     DOI： 10.1021/ja8024966

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  21 in total

Review 1.  Recent advances in azaborine chemistry.

Authors:  Patrick G Campbell; Adam J V Marwitz; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-29       Impact factor: 15.336

2.  Boron in disguise: the parent "fused" BN indole.

Authors:  Eric R Abbey; Lev N Zakharov; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2011-07-13       Impact factor: 15.419

3.  Electrophilic aromatic substitution of a BN indole.

Authors:  Eric R Abbey; Lev N Zakharov; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2010-11-02       Impact factor: 15.419

4.  Nucleophilic aromatic substitution reactions of 1,2-dihydro-1,2-azaborine.

Authors:  Ashley N Lamm; Edward B Garner; David A Dixon; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

5.  Photoisomerization of 1,2-dihydro-1,2-azaborine: a matrix isolation study.

Authors:  Sarah A Brough; Ashley N Lamm; Shih-Yuan Liu; Holger F Bettinger
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-28       Impact factor: 15.336

6.  Negishi Cross-Coupling Is Compatible with a Reactive B-Cl Bond: Development of a Versatile Late-Stage Functionalization of 1,2-Azaborines and Its Application to the Synthesis of New BN Isosteres of Naphthalene and Indenyl.

Authors:  Alec N Brown; Bo Li; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2015-07-09       Impact factor: 15.419

7.  Accessing 1,2-Substituted Cyclobutanes through 1,2-Azaborine Photoisomerization.

Authors:  Zachary X Giustra; Xinyu Yang; Min Chen; Holger F Bettinger; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-07       Impact factor: 15.336

8.  A convergent, modular approach to functionalized 2,1-borazaronaphthalenes from 2-aminostyrenes and potassium organotrifluoroborates.

Authors:  Steven R Wisniewski; Courtney L Guenther; O Andreea Argintaru; Gary A Molander
Journal:  J Org Chem       Date:  2013-12-11       Impact factor: 4.354

9.  BN/CC isosteric compounds as enzyme inhibitors: N- and B-ethyl-1,2-azaborine inhibit ethylbenzene hydroxylation as nonconvertible substrate analogues.

Authors:  Daniel H Knack; Jonathan L Marshall; Gregory P Harlow; Agnieszka Dudzik; Maciej Szaleniec; Shih-Yuan Liu; Johann Heider
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-28       Impact factor: 15.336

10.  The Dewar Isomer of 1,2-Dihydro-1,2-azaborinines: Isolation, Fragmentation, and Energy Storage.

Authors:  Klara Edel; Xinyu Yang; Jacob S A Ishibashi; Ashley N Lamm; Cäcilia Maichle-Mössmer; Zachary X Giustra; Shih-Yuan Liu; Holger F Bettinger
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-30       Impact factor: 15.336
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