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

Arthur J. Ashe; Wolfram Klein; Roger Rousseau

doi:10.1021/om00032a051

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

Arthur J. Ashe, Wolfram Klein, Roger Rousseau

Pacific Northwest National Laboratory

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56 Citations (Scopus)

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, O_1/2, 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 language	English
Pages (from-to)	3225-3231
Number of pages	7
Journal	Organometallics
Volume	12
Issue number	8
DOIs	https://doi.org/10.1021/om00032a051
Publication status	Published - Jan 1 1993

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ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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Ashe, A. J., Klein, W., & Rousseau, R. (1993). Evaluation of the Aromaticity of Borepin: Synthesis and Properties of 1-Substituted Borepins. Organometallics, 12(8), 3225-3231. https://doi.org/10.1021/om00032a051

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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.",

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N2 - 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.

AB - 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.

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10.1021/om00032a051