Photochemistry of Epoxynaphthoquinones. 8. Endo-Stereoselective Photocycloaddition of 2,3-Epoxy-2,3-dihydro-2,3-dimethyl-1,4-naphthoquinone to Olefins Containing Amide Group

DOI: 10.1246/bcsj.60.1021

Source and publish data:

Bulletin of the Chemical Society of Japan p. 1021 - 1026 (1987)

Update date:2022-08-16

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Authors:

Maruyama, Kazuhiro

Osuka, Atsuhiro

Nakagawa, Katsuhiko

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Article abstract of DOI:10.1246/bcsj.60.1021

Irradiation of a benzene solution of 2,3-epoxy-2,3-dihydro-2,3-dimethyl-1,4-naphthoquinone with olefins containing amide group, i.e., N-substituted acrylamides and N-allylcarboxamides predominantly gave the endo-cycloadducts.Upon further irradiation, the cycloadducts underwent photorearrangement to give spirophthalides and alkylidenephthalides.

Full text of DOI:10.1246/bcsj.60.1021

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