One-Step Conversion of Alcohols into Nitriles with Simultaneous Two-Carbon Chain Elongation. (Cyanomethyl)trimethylphosphonium Iodide as a Reagent with a Dual Mode of Action

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Abstract

Treatment of alcohols with an excess of (cyanomethyl)trimethylphosphonium iodide leads, after aqueous hydrolysis, to the clean formation of nitriles with two more carbon atoms than present in the original alcohol. Benzylic, allylic, and aliphatic alcohols without β-branching (RCH₂CH₂OH) have been converted to nitriles with success. The required phosphonium iodide is simple to prepare and can be stored for a long time at room temperature.

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

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  N1-Substituent Effects in the Selective Delivery of Polyamine Conjugates into Cells Containing Active Polyamine Transporters

  Richard Andrew Gardner, Jean-Guy Delcros, Fanta Konate, Fred Breitbeil III, Bénédicte Martin, Michael Sigman, Min Huang, and Otto Phanstiel IV
  Journal of Medicinal Chemistry2004 47 (24), 6055-6069

  • N¹-Substituent Effects in the Selective Delivery of Polyamine Conjugates into Cells Containing Active Polyamine Transporters

    Richard Andrew Gardner, Jean-Guy Delcros, Fanta Konate, Fred Breitbeil III, Bénédicte Martin, Michael Sigman, Min Huang, and Otto Phanstiel IV
    Journal of Medicinal Chemistry2004 47 (24), 6055-6069

    Several N1-arylalkylpolyamines containing various aromatic ring systems were synthesized as their respective HCl salts. The N1-substituents evaluated ranged in size from N1-benzyl, N1-naphthalen-1-ylmethyl, N1-2-(naphthalen-1-yl)ethyl, N1-3-(naphthalen-1-...

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• 

  Dimethylmalonyltrialkylphosphoranes:  New General Reagents for Esterification Reactions Allowing Controlled Inversion or Retention of Configuration on Chiral Alcohols

  James McNulty, Alfredo Capretta, Vladimir Laritchev, Jeff Dyck, and Al J. Robertson
  The Journal of Organic Chemistry2003 68 (4), 1597-1600

  • Dimethylmalonyltrialkylphosphoranes:  New General Reagents for Esterification Reactions Allowing Controlled Inversion or Retention of Configuration on Chiral Alcohols

    James McNulty, Alfredo Capretta, Vladimir Laritchev, Jeff Dyck, and Al J. Robertson
    The Journal of Organic Chemistry2003 68 (4), 1597-1600

    A new class of trialkylphosphorane has been prepared through reaction of a trialkylphosphine with 2-chlorodimethylmalonate in the presence of triethylamine. These new reagents promote the condensation reaction of carboxylic acids with alcohols to provide ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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