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

Article abstract of DOI:10.1021/jo00349a007

The base-promoted reaction of dimethyl (diazomethyl)phosphonate (8) with aldehydes and aryl ketones at low temperatures has been investigated.Alkynes, in modest to excellent yields, are the predominant products of these reactions, a result consistent with the intervention of diazoethenes (3).The latter appear to be unstable toward unimolecular decomposition at -78 deg C and yield nitrogen and alkylidenecarbenes (1).