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Trifluoroacetic anhydride-catalyzed oxidation of isonitriles by DMSO: a rapid, convenient synthesis of isocyanates.

ABSTRACT: A smooth and efficient oxidation of isonitriles to isocyanates by sulfoxides is catalyzed by trifluoroacetic anhydride. With use of DMSO as the oxidant and 5 mol·% TFAA (dichloromethane, -60 to 0 °C), the process is complete in a few minutes, forming dimethyl sulfide as the only byproduct. The newly formed isocyanates may be used directly or isolated in high purity by solvent evaporation.

SUBMITTER: Le HV

PROVIDER: S-EPMC3102642 | biostudies-literature | 2011 May

REPOSITORIES: biostudies-literature

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Trifluoroacetic anhydride-catalyzed oxidation of isonitriles by DMSO: a rapid, convenient synthesis of isocyanates.

Le Hoang V HV Ganem Bruce B

Organic letters 20110414 10

A smooth and efficient oxidation of isonitriles to isocyanates by sulfoxides is catalyzed by trifluoroacetic anhydride. With use of DMSO as the oxidant and 5 mol·% TFAA (dichloromethane, -60 to 0 °C), the process is complete in a few minutes, forming dimethyl sulfide as the only byproduct. The newly formed isocyanates may be used directly or isolated in high purity by solvent evaporation. ...[more]

PMID: 21491899

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