The Journal of Organic Chemistry

Photochemistry of epoxyquinone. 4. Primary dimers in the photochemical reaction of 2, 3-dimethyl-2, 3-epoxy-2, 3-dihydro-1, 4-naphthoquinone

K Maruyama, A Osuka

Index: Maruyama, Kazuhiro; Osuka, Atsuhiro Journal of Organic Chemistry, 1980 , vol. 45, # 10 p. 1898 - 1901

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Citation Number: 11

Abstract

Photolysis of a benzene solution of 2, 3-dimethyl-2, 3-epoxy-2, 3-dihydro-1, 4- naphthoquinone (I)(0.1 M) gave the primary dimers 2a and 2b in 65 and 20% yields, respectively. Upon further irradiation, the primary dimers underwent photoisomerization to give alkylidenephthalide dimers 3a and 3b quantitatively. On the other hand, photolysis of an extremely dilute solution of 1 (< 0.1 mM in benzene) gave different phthalides, 4a and ...