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Synthetic Organic Photochemistry pp 425–487Cite as

Photochemical Synthesis of Oxetans

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Abstract

The photoaddition of benzaldehyde to 2-methylbut-2-ene in sunlight to give an oxetan (Scheme 1) represents one of the pioneering experiments in photochemistry, reported in 1909 by Paterno and Chieffi.(l) This synthesis went unnoticed until 1954 when Büchi and co-workers(2) investigated the scope of the reaction and were able to confirm the structure of the oxetan adduct as 1. Since that date, the production of oxetans by photocycloaddition of carbonyl compounds to alkenes has been the subject of much research; hundreds of examples are known, and the scope and limitations of the reaction are now fairly well understood.(3,4)

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  1. Department of Chemistry, Birkbeck College, University of London, Malet Street, London, WC1E 7HX, UK

    Howard A. J. Carless

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  1. Department of Chemistry, The University of Dundee, DD1 4HN, Dundee, UK

    William M. Horspool

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© 1984 Plenum Press, New York

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Carless, H.A.J. (1984). Photochemical Synthesis of Oxetans. In: Horspool, W.M. (eds) Synthetic Organic Photochemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-2681-6_8

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