Synthetic Photochemistry. LX. One-pot Formation of Spirocyclic 3-Acetyl-2-hydroxy-2-cyclopentenone Derivatives from Methylenecycloalkanes and Methyl 2,4-Dioxopentanoate

DOI: 10.1246/bcsj.66.870

Source and publish data:

Bulletin of the Chemical Society of Japan p. 870 - 876 (1993)

Update date:2022-08-17

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Authors:

Hatsui, Toshihide

Ikeda, Shin-ya

Takeshita, Hitoshi

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Article abstract of DOI:10.1246/bcsj.66.870

A series of proto-photocycloadducts of methyl 2,4-dioxopentanoate to methylenecycloalkanes and -alkenes spontaneously caused retro-benzilic acid rearrangement in high yields.The results are utterly different from those of sterically-crowded acyclic alkenes, with which the rearrangement occurred by thermolysis as a minor process.

Full text of DOI:10.1246/bcsj.66.870

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