Paternò–Büchi reaction

From Wikipedia, the free encyclopedia
  (Redirected from Paterno–Büchi reaction)
Jump to: navigation, search
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] [3]

With substrates benzaldehyde and 2-methyl-2-butene the reaction product is a mixture of structural isomers:

unsymmetric reaction

Another substrate set is benzaldehyde and furan [4]

References[edit]

  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. 
  4. ^ Paternò–Büchi Reaction as a Demonstration of Chemical Kinetics and Synthetic Photochemistry Using a Light Emitting Diode Apparatus Matthew P. Thompson, Jonathan Agger, and Lu Shin Wong Journal of Chemical Education 2015 92 (10), 1716-1720 doi:10.1021/acs.jchemed.5b00129