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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

Florencio Zaragoza*

*Novo Nordisk A/S, Novo Nordisk Park, DK-2760 Malov (Denmark), Email: flonovonordisk.com

F. Zaragoza, J. Org. Chem, 2002, 67, 4963-4964.

DOI: 10.1021/jo025731r


Abstract

Benzylic, allylic, and aliphatic alcohols without β-branching have been converted to nitriles with two more carbon atoms than present in the substrate by treatment with an excess of (cyanomethyl)trimethylphosphonium iodide and subsequent in situ hydrolysis of the intermediate C-alkylated (cyanomethyl)phosphonium salts.

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proposed mechanism



Key Words

Nitriles


ID: J42-Y2002-000