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Photochemistry of 9-Vinyl Substituted Anthracenes of Their Reduced Derivatives and of Diels Alder Type Adducts of 9-Vinylanthracenes With Activated Dienophiles
1 , * 1 , 1 , 2 , 3 , 4
1  Department of Chemistry, United Arab Emirates University, Al Ain, UAE
2  Department of Chemical Engineering, UAEU
3  Institute of Inorganic Chemistry, University of Hamburg
4  Department of Applied Chemical Sciences, Jordan University of Science & Technology

Abstract: The photochemistry of the vinyl substituted (E)-3-(anthran-9-yl)propenoates and (E)-9-(aroylethenyl)anthracenes as well of their reduced derivatives has been studied at lambda = 254 nm and at lambda= 352 nm. At lambda = 254 nm and lambda= 352 nm, the 9-vinyl substituted anthracenes undergo E/Z-isomerization, while their reduced derivatives undergo [4+4]-dimerisation reactions at lamda = 352 nm. An X-ray crystal structure shows the [4+4]-photoadducts to be head-to-tail. The photochemistry of cycloadducts of (E)-3-(anthran-9-yl)propenoates and (E)-9-(aroylethenyl)anthracenes with maleimides and other activated dienophiles show a number of reactions, among them retro-cleavage of the cycloadducts to the respective anthracenes.
Keywords: photochemistry; [4+4]-dimerisation; anthracenes; photochemical E/Z isomerisation