The Paternò–Büchi reaction, named after Emanuele Paternò and George Büchi, who established its basic utility and form,[1][2] is a photochemical reaction, specifically a 2+2 photocycloaddition, which forms four-membered oxetane rings from an excited carbonyl and reacting with an alkene.[3]
| 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 |
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:
Another substrate set is benzaldehyde and furan[4] or heteroaromatic ketones and fluorinated alkenes.[5]
The alternative strategy for the above reaction is called the Transposed Paternò−Büchi reaction.
See also
edit- Aza Paternò−Büchi reaction - the aza-equivalent of the Paternò–Büchi reaction
- Enone–alkene cycloadditions - photochemical reaction of an enone with an alkene to give a cyclobutene ring unit
References
edit- ^ Paterno, E.; Chieffi, G. (1909). "Sintesi in chimica organica per mezzo della luce. Nota II. Composti degli idrocarburi non saturi con aldeidi e chetoni" [Synthesis in organic chemistry by means of light. Note II. Compounds of unsaturated hydrocarbons with aldehydes and ketones]. Gazz. Chim. Ital. (in Italian). 39: 341–361.
- ^ 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.
- ^ 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. S2CID 196714415.
- ^ Thompson, Matthew P.; Agger, Jonathan; Lu Shin Wong (2015). "Paternò–Büchi Reaction as a Demonstration of Chemical Kinetics and Synthetic Photochemistry Using a Light Emitting Diode Apparatus". Journal of Chemical Education. 92 (10): 1716–1720. doi:10.1021/acs.jchemed.5b00129.
- ^ Fernandez, Mario Andrés Gomez; Lefebvre, Corentin; Sudau, Alexander; Genix, Pierre; Vors, Jean-Pierre; Abe, Manabu; Hoffmann, Norbert (2021). "Studies on The Application of The Paternò-Büchi Reaction to The Synthesis of Novel Fluorinated Scaffolds". Chemistry – A European Journal. 27 (63): 15722–15729. doi:10.1002/chem.202102621. ISSN 1521-3765. PMID 34523761. S2CID 237514827.