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

Research output: Contribution to journal › Article › peer-review

67 Scopus citations

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
State	Published - 1993
Externally published	Yes

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@article{94392ce8aa7c4e53a9f977c01902a7dd,

title = "Evaluation of the Aromaticity of Borepin: Synthesis and Properties of 1-Substituted Borepins",

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.",

author = "Ashe, \{Arthur J.\} and Wolfram Klein and Roger Rousseau",

year = "1993",

doi = "10.1021/om00032a051",

language = "English",

volume = "12",

pages = "3225--3231",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "8",

}

TY - JOUR

T1 - Evaluation of the Aromaticity of Borepin

T2 - Synthesis and Properties of 1-Substituted Borepins

AU - Ashe, Arthur J.

AU - Klein, Wolfram

AU - Rousseau, Roger

PY - 1993

Y1 - 1993

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.

UR - https://www.scopus.com/pages/publications/0011457949

U2 - 10.1021/om00032a051

DO - 10.1021/om00032a051

M3 - Article

AN - SCOPUS:0011457949

SN - 0276-7333

VL - 12

SP - 3225

EP - 3231

JO - Organometallics

JF - Organometallics

IS - 8

ER -

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

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