176045-24-2Relevant academic research and scientific papers
Photocyclization Reactions. Part 3 [1]. Synthesis of Naphtho[1,8-bc]-furans and Cyclohepta[cd]benzofurans Using Photocyclization of 8-Alkoxy-1,2,3,4-tetrahydro-1-naphthalenones and 4-Alkoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ones
Sharshira, Essam Mohamed,Iwanami, Haruki,Okamura, Mutsuo,Hasegawa, Eietsu,Horaguchi, Takaaki
, p. 17 - 25 (2007/10/03)
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.
Conformational Effects in Photocyclization of Six and Seven-membered Ring Alkoxyketones
Horaguchi, Takaaki,Iwanami, Haruki,Tanaka, Takakazu,Hasegawa, Eietsu,Shimizu, Takahachi
, p. 44 - 46 (2007/10/02)
Irradiation of 8-alkoxytetrahydro-1-naphthalenones 5 gave rearranged naphthyl alcohols 11 as major products and in contrast, 4-alkoxytetrahydrobenzocyclohepten-5-ones 6 afforded tetrahydrocycloheptabenzofurans 14 in good yields; the difference in reactivities is attributed to the conformation of six- and seven-membered rings.
