Journal of Heterocyclic Chemistry p. 17 - 25 (1996)
Update date:2022-08-05
Topics: Synthesis Experimental Photocyclization Naphtho[1,8-bc]-furans Cyclohepta[cd]benzofurans 1,2,3,4-tetrahydro-1-naphthalenones 4-Alkoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ones
Sharshira, Essam Mohamed
Iwanami, Haruki
Okamura, Mutsuo
Hasegawa, Eietsu
Horaguchi, Takaaki
Photocyclization reactions were carried out on 8-alkoxy-1,2,3,4-tetrahydro-1-naphthalenones (six-membered ring ketones) 4a-g and 4-alkoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ones (seven-membered ring ketones) 5a-e in acetonitrile. Irradiation of 4a-f gave rearranged naphthyl alcohols 8a-f as major products. In the case of 4g, 2a,3,4,5-tetrahydronaphtho[1,8-bc]furan-2a-ol 6g was obtained. In contrast, irradiation of 5a-e afforded 2,2a,3,4,5,6-hexahydrocyclohepta[cd]benzofuran-2a-ols 9a-e in good yields. The difference in reactivities between 4a-g and 5a-e is attributed to the conformation of six- and seven-membered rings. Conformational and substituent effects in cyclization step of 1,5-biradicals are discussed along with reaction pathways.
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