The acid-catalyzed condensation of alkenes with aldehydes is known as the Prins reaction. A protonated aldehyde is attacked by the alkene to afford the most stable β-hydroxyl carbocation that can engage in various reaction pathways dependent on the reaction conditions: (i) Water and a hydrogen atom on the carbon adjacent to the carbocation yield 1,3-diols and/or allylic alcohols, (ii) the presence of a nucleophile creates 3-substituted alcohols, and (iii) excess aldehyde affords 1,3-dioxanes.
- Reagents: Protic or Lewis Acid Catalyst (e.g. H2SO4, HCl, HNO3, AlCl3, BF3, etc.), Solvent (H2O, ROH, Benzene), Nucleophile (Solvent or Conjugate Base of the Protic Acid)
- Reactant: Cyclic or Acyclic Alkene (H, Alkyl, Aryl, or Heteroaryl Substituents), Alkyl or Aryl Aldehyde
- Product: Allylic Alcohol and/or Various Products Dependent on the Nucleophile (3-Substituted Alcohol, Diene, 1,3-Diol, or 1,3-Dioxane)
- Type of Reaction: Condensation
Mechanism
Top Citations
- Focused Update on the Prins Reaction and the Prins Cyclization. Current Organic Chemistry 2012, 16 (10), 1277–1312.
Original Paper
- Prins, H. J. Chem. Weekblad 1919, 16 1072-1073.
Related Reactions
- Alder-Ene reaction
Related Compounds
- Catalytic Acid
- Aldehyde
