Photochemistry of Epoxynaphthoquinones. 8. Endo-Stereoselective Photocycloaddition of 2,3-Epoxy-2,3-dihydro-2,3-dimethyl-1,4-naphthoquinone to Olefins Containing Amide Group
作者:Kazuhiro Maruyama、Atsuhiro Osuka、Katsuhiko Nakagawa
DOI:10.1246/bcsj.60.1021
日期:1987.3
Irradiation of a benzene solution of 2,3-epoxy-2,3-dihydro-2,3-dimethyl-1,4-naphthoquinone with olefins containing amide group, i.e., N-substituted acrylamides and N-allylcarboxamides predominantly gave the endo-cycloadducts. Upon further irradiation, the cycloadducts underwent photorearrangement to give spirophthalides and alkylidenephthalides.
苯溶液中2,3-环氧-2,3-二氢-2,3-二甲基-1,4-萘醌与含有酰胺基的烯烃,即N-取代丙烯酰胺和N-烯丙基羧酰胺的照射主要生成endo-环加成物。进一步照射后,这些环加成物发生光重排,生成螺苯并二氢吡喃酮和烷叉基苯并二氢吡喃酮。