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Amino and Alkyl B-Substituted P-Stabilized Borenium Salts.

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Title: Amino and Alkyl B-Substituted P-Stabilized Borenium Salts.
Authors: Devillard, Marc1, Bouhadir, Ghenwa1, Mallet-Ladeira, Sonia2, Miqueu, Karinne3, Bourissou, Didier1 dbouriss@chimie.ups-tlse.fr
Source: Organometallics. Nov2016, Vol. 35 Issue 21, p3788-3794. 7p.
Subjects: Amino compounds, Alkyl compounds, Borenium ions, Functional groups, Benzene, Solution (Chemistry)
Abstract: The ability of the phosphino-naphthyl moiety to stabilize amino- and alkylborenium cations has been studied. Surprisingly, the phosphine-aminochloroborane precursor 2 was found to exist in neutral open form (without P-B interaction) in benzene solution and in the solid state but to ionize spontaneously in chloroform to generate the P-stabilized borenium salt 3. Addition of gallium trichloride shifts the process forward and affords the corresponding tetrachlorogallate borenium salt 3'. The phosphine group of 2 remains available for external reactivity, as shown by the ready formation of the corresponding phosphine gold(I) chloride complex 4. The P-stabilized cyclohexylborenium cation 6 has also been prepared by reacting the corresponding bromoborane 5 with gallium tribromide. Compound 6 is a very rare example of an alkyl-substituted borenium salt. The structures of 2, 3', and 4-6 have been unambiguously ascertained by multinuclear NMR spectroscopy and X-ray crystallography. [ABSTRACT FROM AUTHOR]
Copyright of Organometallics is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
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DbLabel: Engineering Source
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  Data: Amino and Alkyl B-Substituted P-Stabilized Borenium Salts.
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  Data: <searchLink fieldCode="AR" term="%22Devillard%2C+Marc%22">Devillard, Marc</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Bouhadir%2C+Ghenwa%22">Bouhadir, Ghenwa</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Mallet-Ladeira%2C+Sonia%22">Mallet-Ladeira, Sonia</searchLink><relatesTo>2</relatesTo><br /><searchLink fieldCode="AR" term="%22Miqueu%2C+Karinne%22">Miqueu, Karinne</searchLink><relatesTo>3</relatesTo><br /><searchLink fieldCode="AR" term="%22Bourissou%2C+Didier%22">Bourissou, Didier</searchLink><relatesTo>1</relatesTo><i> dbouriss@chimie.ups-tlse.fr</i>
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  Data: <searchLink fieldCode="JN" term="%22Organometallics%22">Organometallics</searchLink>. Nov2016, Vol. 35 Issue 21, p3788-3794. 7p.
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  Data: <searchLink fieldCode="DE" term="%22Amino+compounds%22">Amino compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Alkyl+compounds%22">Alkyl compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Borenium+ions%22">Borenium ions</searchLink><br /><searchLink fieldCode="DE" term="%22Functional+groups%22">Functional groups</searchLink><br /><searchLink fieldCode="DE" term="%22Benzene%22">Benzene</searchLink><br /><searchLink fieldCode="DE" term="%22Solution+%28Chemistry%29%22">Solution (Chemistry)</searchLink>
– Name: Abstract
  Label: Abstract
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  Data: The ability of the phosphino-naphthyl moiety to stabilize amino- and alkylborenium cations has been studied. Surprisingly, the phosphine-aminochloroborane precursor 2 was found to exist in neutral open form (without P-B interaction) in benzene solution and in the solid state but to ionize spontaneously in chloroform to generate the P-stabilized borenium salt 3. Addition of gallium trichloride shifts the process forward and affords the corresponding tetrachlorogallate borenium salt 3'. The phosphine group of 2 remains available for external reactivity, as shown by the ready formation of the corresponding phosphine gold(I) chloride complex 4. The P-stabilized cyclohexylborenium cation 6 has also been prepared by reacting the corresponding bromoborane 5 with gallium tribromide. Compound 6 is a very rare example of an alkyl-substituted borenium salt. The structures of 2, 3', and 4-6 have been unambiguously ascertained by multinuclear NMR spectroscopy and X-ray crystallography. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
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  Data: <i>Copyright of Organometallics is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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      – Type: doi
        Value: 10.1021/acs.organomet.6b00737
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      – Code: eng
        Text: English
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        PageCount: 7
        StartPage: 3788
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      – SubjectFull: Amino compounds
        Type: general
      – SubjectFull: Alkyl compounds
        Type: general
      – SubjectFull: Borenium ions
        Type: general
      – SubjectFull: Functional groups
        Type: general
      – SubjectFull: Benzene
        Type: general
      – SubjectFull: Solution (Chemistry)
        Type: general
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      – TitleFull: Amino and Alkyl B-Substituted P-Stabilized Borenium Salts.
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              Text: Nov2016
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              Y: 2016
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