Photoadducts of 1-cyclohexene-1, 2-dicarboxylic anhydride

…, EK Fields, S Meyerson, ME Wright…

Index: Nimry, T.S.; Fields, E.K.; Meyerson, Seymour; Wright, M.E.; Hall, H.K. Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 4102 - 4104

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Abstract

1-Cyclohexene- 1,2-dicarboxylic anhydride (I) reacts with butadiene, isoprene, and dimethylbutadiene only under vigorous conditions (12 hours at 175 "C) to give 50-60% yields of thermal [2 + 41 adducts.'r2 It does not react even at 175 "C with furan, chloroprene, or cyclopentadiene.2 We have found that, in contrast to its reluctance to undergo thermal cycloaddition, I reacts readily with a variety of olefins under irradiation with weak ultraviolet light at 25-80 "C to give [2 + ...