Bobbitt's Salt-Mediated Oxidation of Alkynyl-ols and -diols to the Corresponding Aldehydes and Their Application in...

Propargyl alcohol derivatives were readily oxidized using Bobbitt's salt to yield the corresponding propynal products. 2-Butyn-1,4-diol may be selectively oxidized to provide either 4-hydroxy-2-butynal or acetylene dicarboxaldehyde, and the resulting stable dichloromethane solutions containing the chemically sensitive acetylene aldehydes were used directly in subsequent Wittig, Grignard, or Diels-Alder reactions. This method provides safe and efficient access to propynals and allows the preparation of polyfunctional acetylene compounds from readily accessible starting material without the use of protecting groups.