Evaluation of the Aromaticity of Borepin: Synthesis and Properties of 1-Substituted Borepins

Arthur J. Ashe, Wolfram Klein, Roger Rousseau

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Abstract

The reaction of 1,1-dibutylstannepin with BCl3 gave 1-chloroborepin, which has been converted to a variety of 1-substituted borepins, C6H6BX, where X = OH, O1/2, OCH3, 2,4,6-Me3C6H2, CH2CH2CH2NMe2, F, NH2, N(CH2)5, N(iPr)2, H. 1-Chloroborepin and 1-aminoborepin have been investigated by ab initio methods. All borepins have been studied using 1H NMR, 11B NMR, and 13C NMR spectroscopy. The X-ray crystal structure of 1-chloroborepin gives evidence of a π-delocalized structure. All properties are discussed in terms of the aromatic character of the borepin ring system.

Original languageEnglish
Pages (from-to)3225-3231
Number of pages7
JournalOrganometallics
Volume12
Issue number8
DOIs
Publication statusPublished - Jan 1 1993

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ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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