N-Isocyanotriphenyliminophosphorane; a Convenient Reagent for the Conversion of Acyl Chlorides into α-Diazoketones

Enrique Aller; Pedro Molina; Ángeles Lorenzo

doi:10.1055/s-2000-6576

Synlett 2000; 2000(4): 526-528
DOI: 10.1055/s-2000-6576

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N-Isocyanotriphenyliminophosphorane; a Convenient Reagent for the Conversion of Acyl Chlorides into α-Diazoketones

Enrique Aller^* , Pedro Molina, Ángeles Lorenzo

^*Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, Campus de Espinardo, E-30071 Murcia, Spain; Fax +3 49 68 36 41 49; E-mail: pmolina@fcu.um.es

Abstract

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Aliphatic, aromatic and vinylic acid chlorides were converted into the corresponding α-diazoketones in synthetically useful yields by reaction with N-isocyanotriphenyliminophosphorane followed by treatment of the resulting N-unsubstituted α-ketohydrazidoyl chlorides with triethylamine in the presence of a catalytic amount of p-toluenesulfonyl chloride.

acyl chlorides - α-diazoketones - N-isocyanotriphenyliminophosphorane - α-ketohydrazidoyl chlorides

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