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Mechanism of the photo-rearrangement of aryl-6,7-dioxabicyclo[3.2.2]nona-3,8-dien-2-one into tricyclic lactone

✍ Scribed by T. Tezuka; R. Miyamoto; M. Nagayama; T. Mukai

Publisher: Elsevier Science
Year: 1975
Tongue: French
Weight: 226 KB
Volume: 16
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)71855-7

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✦ Synopsis

It has been shown that the enone-x interaction (shown by a) is inherent to the excited state of homoconjugated cyclic dienones (la-h), which brings about the photo-Cope rearrangement probably through thier singlet states, giving rise to the formation of theketenes(2ah h)(1,2,3). Recently, however, Sasaki and co-workers have reported that in the dienone (Ii) the enone-lone pair electrons interaction (shown by by) competed with the enone-n interaction giving rise to the formation of 1 (or 3i) along with 2 (or i)(4).

Some time ago we reported a novel photo-rearrangement of & and B into 2 and 2, respectively

(5).

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