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Trimethylsilyldiazomethane in the preparation of diazoketones via mixed anhydride and coupling reagent methods: a new approach to the Arndt-Eistert synthesis

Jožko Cesar and Marija Sollner Dolenc

*Faculty of Pharmacy, University of Ljubljana, Askerceva 7, 1000, Ljubljana, Slovenia, Email:

J. Cesar, M. Sollner Dolenc, Tetrahedron Lett., 2001, 42, 7099-7102.

DOI: 10.1016/S0040-4039(01)01458-7

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Reaction of trimethylsilyldiazomethane with a mixed anhydride derived from a carboxylic acid and ethyl chloroformate yields the corresponding diazoketone in high yield. Subsequent Wolff rearrangement of the diazoketone leads to the homologated ester. Reactions of trimethylsilyldiazomethane with convenient active esters are described.

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Key Words

trimethylsilyldiazomethane, Arndt-Eistert synthesis, mixed anhydrides, diazoketones, Wolff rearrangement, dicyclohexylcarbodiimide, N-hydroxysuccinimide

ID: J72-Y2001-620