Diazoethenes: their attempted synthesis from aldehydes and aromatic ketones by way of the Horner-Emmons modification of the Wittig reaction. A facile synthesis of alkynes

J. C. Gilbert, U. Weerasooriya

*Department of Chemistry, The University of Texas at Austin, Austin, Texas 78712

J. C. Gilbert, U. Weerasooriya, J. Org. Chem., 1982, 47, 1837-1845.

DOI: 10.1021/jo00349a007

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Abstract

The base-promoted reaction of dimethyl (diazomethyl)phosphonate with aldehydes and aryl ketones at low temperatures gives alkynes in good yields. This result is consistent with the intervention of diazoethenes that appear to be unstable toward unimolecular decomposition.

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Key Words

Seyferth-Gilbert Homologation, Alkynes

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ID: J54-Y1982-130