Paternò–Büchi reaction

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Here an electronically excited carbonyl group is added to a ground state olefin yielding an oxetane.

The Paternò–Büchi reaction, named after Emanuele Paternò and George Büchi who established its basic utility and form, is a photochemical reaction that forms four-membered oxetane rings from a carbonyl and an alkene.[1][2]

Much work has been done with the reaction since Dr. Thorsten Bach of the Technical University Munich published a review article in 1998 on its mechanism and synthetic utility.[3]

The Paternò–Büchi reaction has been used recently in attempt to synthesize many natural organic products. In these experiments, the chemists are chiefly concerned with the regio- and diastereoselectivity of the products.

References

  1. ↑ E. Paterno, G. Chieffi (1909). ".". Gazz. Chim. Ital. 39: 341. 
  2. ↑ G. Büchi, Charles G. Inman, and E. S. Lipinsky (1954). "Light-catalyzed Organic Reactions. I. The Reaction of Carbonyl Compounds with 2-Methyl-2-butene in the Presence of Ultraviolet Light". Journal of the American Chemical Society 76 (17): 4327–4331. doi:10.1021/ja01646a024. 
  3. ↑ Thorsten Bach (1998). "Stereoselective Intermolecular [2 + 2]-Photocycloaddition Reactions and Their Application in Synthesis". Synthesis 1998: 683–703. doi:10.1055/s-1998-2054. 
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