Stepwise Bond Formation in Photochemical and Thermal Diels-Alder Reactions of C60 with Danishefsky's Dienes

…, S Matsumoto, Y Okubo, M Fujitsuka, O Ito…

Index: Mikami, Koichi; Matsumoto, Shoji; Okubo, Yasutaka; Fujitsuka, Mamoru; Ito, Osamu; Suenobu, Tomoyoshi; Fukuzumi, Shunichi Journal of the American Chemical Society, 2000 ,  vol. 122,  # 10  p. 2236 - 2243

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Citation Number: 41

Abstract

Mechanisms of both the photochemical and thermal Diels-Alder reactions of C60 with Danishefsky's dienes are studied on the basis of product stereochemistry, kinetics, and the detection of radical intermediates. A stereochemically defined (1 E, 3 Z)-1-methoxy-2-methyl- 3-[(trimethylsilyl) oxy]-penta-1, 3-diene (1a) is used as a stereochemical probe in the Diels- Alder reactions with C60. The major Diels-Alder product is trans-adduct (3) rather than cis- ...