論文第一部份主要是利用4-甲氧基酚57與二乙醯基亞碘苯(DAIB)在甲醇中反應合成出掩飾對苯醌46，再將掩飾對苯醌在路易士酸MAD [methyl aluminium bis(2, 6-di-tert-butyl-4-methylphenoxide)]螯合下，利用格林那試劑進行1, 4-加成反應，得到4, 4-二甲氧基-5-（4-取代苯基）-2-環己烯酮58, 59, 60。
第二部分則是利用合成出的化合物58, 59, 60分別配置成低濃度(0.01 M)的三氟乙醇溶液後，再利用352 nm波長的光源進行照光反應。化合物58, 59, 60照光可獲得五員環縮環產物61, 62, 63, 64, 66, 67，化合物60照光可獲得四員環縮環產物65a+65b，進而討論其反應機構。

This thesis deals with the synthesis of 4, 4-dimethoxy-5-(4-substituted- phenyl)-cyclohex-2-enones 58, 59, 60 via 1, 4-addition of Grignard reagents to 4, 4-dimethoxycyclohexa-2, 5-dienone 46. These compounds 58, 59, 60 are
irradiated in trifluoroethanol (0.01M) with light of 352 nm to give cyclopentanone
derivatives 61, 62, 63, 64, 66, 67. However, irradiation of 4, 4-dimethoxy- 5- (4-methoxyphenyl)-cyclohex-2-enone60 gives a mixture cyclobutanone
derivative 65a+65b as well.

中文摘要..........................I
英文摘要..........................II
謝誌.............................III
縮寫對照表.........................IV
目錄...............................V
表目錄.............................VIII
圖目錄.............................IX
第一章 緒論..........................1
1.1 有機光化學概論....................1
1.2 共軛烯酮光化學概論................3
1.3 環己烯酮的照光重排反應及反應機構....5
1.4 研究構思.........................10
第二章 結果與討論.....................13
2.1 化合物的合成......................13
2.1.1 4, 4-二甲氧基-2,5-環己二烯酮的合成..13
2.1.2 4, 4-二甲氧基-5-（4-取代苯基）-2-環己烯酮衍生物的合成...13
2.1.3合成產物結構鑑定...................14
2.2 化合物的照光反應....................16
2.2.1 4, 4-二甲氧基-5-（4-取代苯基）-2-環己烯酮衍生物的照光反應.....................................16
2.2.2 照光產物立體結構鑑定..............18
2.2.3照光產物spirobutenolide的生成......33
2.3 結論 ..............................34
第三章 實驗部份........................36
3.1 一般實驗方法......................36
3.2 實驗步驟及光譜資料.................38
3.2.1 化合物58的合成..................38
3.2.2 化合物59的合成..................39
3.2.3 化合物60的合成..................41
3.2.4 化合物58的照光反應...............42
3.2.5 化合物59的照光反應...............44
3.2.6 化合物60的照光反應...............46
第四章 參考文獻........................50
附錄一 化合物的光譜圖...................54

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