Details

Autor(en) / Beteiligte

• Bobbitt, James M.
• Eddy, Nicholas A.
• Brückner, Christian
• Bailey, William F.
• Merbouh, Nabyl

Titel

Bobbitt’s Salt-Mediated Oxidation of Alkynyl-ols and -diols to the Corresponding Aldehydes and Their Application in Tandem Reactions

Ist Teil von

• Journal of organic chemistry, 2023-03, Vol.88 (5), p.3321-3325

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2023

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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.