Intramolecular Photochemical Reactions of 4-(ω-Alkenyloxy)-6-methyl-2-pyrones Having an Alkoxycarbonyl Group at the Olefinic Carbon Chain

DOI: 10.1021/jo00025a035

Source and publish data:

Journal of Organic Chemistry p. 7150 - 7154 (1991)

Update date:2022-08-16

Topics:

Authors:

Shimo, Tetsuro

Tajima, Jun

Suishu, Takaaki

Somekawa, Kenichi

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Article abstract of DOI:10.1021/jo00025a035

Photochemical reactions of 4-(ω-alkenyloxy)-6-methyl-2-pyrones 4-8 were investigated.Photosensitized reactions of 2-pyrones 4-6 gave intramolecular <2 + 2> cycloadducts 14-16 as oxatricyclic lactones, site-, regio- and stereospecifically, but 7 and 8 gave no products.On the other hand, direct irradiations of 4 and 5 afforded cyclobutenecarboxylic acids 19 and 20, respectively.The intramolecular cycloaddition mechanism was also explained from the excited state of 2-pyrone calculated by means of the MNDO-CI method.

Full text of DOI:10.1021/jo00025a035

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