✦ LIBER ✦

Photolysis of dibenzocycloocta-1,4-diene-6-diazo-3,7-dione in methanol. Intramolecular trapping of the Wolff rearranged product by photochemically formed hydroxyl group

✍ Scribed by Hideo Tomioka; Kohji Kawaguchi

Publisher: Elsevier Science
Year: 1995
Tongue: English
Weight: 312 KB
Volume: 87
Category: Article
ISSN: 1010-6030
DOI: 10.1016/1010-6030(94)04001-i

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✦ Synopsis

Irradiation (A>3(Y0 nm) of dibenzocycloocta-l,4-diene-6-diazo-3,7-dione in methanol gave a bicyclic lactone as the sole isolable product. This can be explained in terms of intramolecular lactonization by attack of the hydroxyl group (produced as a result of the photoaddition of methanol on the excited carbonyl group at the 3 position) on the methoxycarbonyl group (Ik)rmed by Wolff rearrangement followed by nucleophilic attack of the solvent).