Jump to content

Paternò–Büchi reaction

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by Monkbot (talk | contribs) at 12:34, 11 December 2020 (Task 18 (cosmetic): eval 3 templates: del empty params (5×);). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Paternò–Büchi reaction
Named after Emanuele Paternò
George Büchi
Reaction type Ring forming reaction
Identifiers
Organic Chemistry Portal paterno-buechi-reaction
RSC ontology ID RXNO:0000083

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 an excited carbonyl and reacting with an alkene.[1] [2] [3]

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

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]

The alternative strategy for the above reaction is called the Transposed Paternò−Büchi reaction.

The aza-equivalent of the above reactoin is the Aza Paternò−Büchi reaction.

References

  1. ^ E. Paterno, G. Chieffi (1909). Gazz. Chim. Ital. 39: 341. {{cite journal}}: Missing or empty |title= (help)
  2. ^ G. Büchi; Charles G. Inman; 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 (5): 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