本論文研究掩飾鄰苯醌與單態氧的化學反應。主要探討不同取代基的掩飾鄰苯醌22a-j與單態氧反應之類型：Diels-Alder反應和特殊的重排反應。並討論其可能的反應機構。選用兩種染料/溶劑系統：Rose Bengal/ 甲醇和TPP/ 氘氯仿，推論出CDCl3偏好雙自由基中間體而形成 [4+2] 產物；以及在甲醇偏好能量較高的perepoxide的中間體而形成五環烯酮產物。但是22i和22j沒有這樣的溶劑選擇性，全部得到[4+2] 產物。掩飾鄰苯醌22e，經過與單態氧的反應之後，預期可得到天然物Untenone A 24e。

This thesis is concerned with the chemical reaction between MOB and singlet oxygen and deals with the reaction types of MOBs 22a-j and singlet oxygen: Diels-Alder reaction and rearrangement. This thesis is also looking into their possible mechanisms. We have chosen two sensitizers/ solvent systems which are Rose Bengal/ methanol and TPP/ d-chloroform and concluded that d-chloroform preferred the intermediate of biradical to form [4+2] adduct. Furthermore, methanol preferred the intermediate of perepoxide which contains higher energy to form cyclopentenone. However, without such solvent selectivity, 22i and 22j with singlet oxygen produce [4+2] adducts 26i and 26j completely both in d-chloroform and methanol . In the future, after MOB 22e reacts with singlet oxygen, the formation of natural product, Untenone A 24e, can be expected.

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