Paterno-Buchi reaction

Paterno-Buchi reaction

The Paternò–Büchi reaction, named after Emanuele Paternò and George Hermann Büchi who established its basic utility and form, is a photochemical reaction that forms four-membered oxetane rings from a carbonyl and an alkene. [cite journal
title = .
author = E. Paterno, G. Chieffi
journal = Gazz. Chim. Ital.
volume = 39
issue =
pages = 341
year = 1909
url =
doi = ] [cite journal
title = Light-catalyzed Organic Reactions. I. The Reaction of Carbonyl Compounds with 2-Methyl-2-butene in the Presence of Ultraviolet Light
author = G. Büchi, Charles G. Inman, and E. S. Lipinsky
journal = Journal of the American Chemical Society
volume = 76
issue = 17
pages = 4327–4331
year = 1954
url =
doi = 10.1021/ja01646a024 ]

Much work has been done with the reaction since Dr. Thorsten Bach of the University of Marburg published a review article in 1998 on its mechanism and synthetic utility. [cite journal
title = Stereoselective Intermolecular [2 + 2] -Photocycloaddition Reactions and Their Application in Synthesis
author = Thorsten Bach
journal = Synthesis
volume = 1998
issue =
pages = 683–703
year = 1998
url =
doi = 10.1055/s-1998-2054 ]

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


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