Abstract
Abstract In this thesis we have studied the photochemical reactions of (1S*,2R*,6S*,7R*)-tricyclo[5.2.2.02,6]undeca-4,10-dien-8-ones 48 and 51 which were synthesized by following the methodology developed in our laboratory. A variety of 2-methoxyphenols were oxidized using diacetoxyiodobenzene [PhI(OAc)2] to generate masked o-benzoquinones and the subsequent Diels-Alder reaction with cyclopentadiene produced the cycloadducts 48. The dienones 51 were obtained by the SmI2 catalyzed reduction of two methoxy groups of 48. The photochemical reactions of 51 were studied by making clear solutions in benzene . The 1% benzene solutions of dienones 48 and 51 underwent photolysis at 300 nm to afford the products 57 and 65. The Norrish type I products 58 were also formed by decarbonylation. The compounds 57 and 65 upon addition of vinyl magnesium bromide produced the compounds 72 and 73. Neither [1,3]-sigmatropic rearrangement products 74 and 75 nor [3,3]-sigmatropic rearrangement products 76 were obtained. When 72a,b were heated in vacuum sealed tube at 160℃ for 8h under neutral conditions in mesitylene compounds 77a,b were obtained.