Abstract
摘 要本論文目的在於研究掩飾苯□與各種親雙烯劑的Diels-Alder反應， 分為兩部份：第一部份討論以二乙醯基亞碘苯 (iodobenzene diacetate ；IBD) 將6-甲氧基-4-(2,5-二□環戊基)酚39氧化成掩飾鄰苯□40，再與 丙烯酸甲酯、甲基丙烯酸甲酯、甲基乙烯基酮、苯乙烯基、乙烯基硫醚、 苯甲基乙烯基醚等各種親雙烯劑進行分子間Diels-Alder反應，生成雙環 [2.2.2]辛烯酮化合物36、42~46，產率88%~62%。第二部份討論以二乙醯 基亞碘苯 (iodobenzene diacetate, IBD) 將甲基5-(3,5-己二烯氧 基)-2-羥基苯甲酸酯71~73氧化成掩飾對苯□74，亦可以雙-三氟乙醯基亞 碘苯 (iodobenzene bis(trifluroroacetate), PIFA) 為氧化劑，將甲 基2-羥基-5-甲氧基苯甲酸酯83與共軛雙烯醇65~67氧化而得掩飾對苯□74 後，進行分子內Diels-Alder反應，生成順式-十□氫化合物75~82。 AbstractThis thesis describes the studies on inter- and intra- molecular Diels-Alder reactions of masked benzoquinones.The first part describes intermolecular Diels-Alder reactions of masked benzoquinone 40. Oxidation of phenol 39 with IBD provided masked o-benzoquinone 40, which reacted with dienophiles such as methyl acrylate, methyl methacrylate, methyl vinyl kentone, styrene, phenyl vinyl thioether and benzyl vinyl ether to afford the bicyclo[2.2.2]octa-5-ene-2-ones compounds 36, 42~46.The second part delineate intramolecular Diels-Alder reactions of masked p-benzoquinone 74. Oxidation of phenol 71~73 with IBD in methanol or oxidation of phenol 83 contain PIFA in presence of 3,5-dienols 65~67 in dichloromathane provided masked p- benzoquinone 25. The intramolecular Diels-Alder reactions of 74 afforded the cis-decalin derivatives 75~82.