自由基反應發展至今，已廣泛被應用在碳-碳鍵的生成，而自由基的
環合反應已經成為合成雜環化合物的方法之一。常見的有利用醋酸錳（III）或是硝酸鈰銨（IV），來進行氧化性自由基反應。另外，銀（II）雖然價格昂貴，但僅需使用催化劑量就可進行自由基反應，因此可朝綠色化學方向研究。本篇想要利用氧化性自由基環合反應來合成具有吡咯環的1,4-醌類化合物。
本篇報告主要分為兩部分：
第一部分為利用醋酸錳（III）的氧化性自由基反應生成碳-氮鍵，合成出吡咯-1,4-醌類化合物；第二部分則是利用硝酸銀與過硫酸鉀作用生成銀（II）離子，再與羧酸化合物作用生成烷基自由基，經由自由基的加成反應來獲得異吡咯-1,4-苯醌類化合物。

Free-radical reaction has been applied to formation of carbon-carbon bond for decades and it plays an important role for synthesis of heterocyclic compounds. Manganese (III) acetate and cerium (IV) ammonium nitrate are
the most common reagents for the oxidative free-radical reaction. Silver (II) can be generated in situ from silver (I) and persulfate and catalytical amount of silver (I) was used, may this meet the requirement of green chemistry. In this thesis, synthesis of the pyrrole ring containing 1,4-naphthoquinones via the oxidative free radical reaction was reported.
This thesis is divided into two parts:
(1) Synthesis of pyrrole-1,4-naphthoquinones via manganese (III) oxidative free-radical reaction which led to formation of carbon-nitrogen bond.
(2) Silver (II) ion is produced by the reaction with silver nitrate and potassium persulfate. Alkyl free-radical generated by oxidation of carboxylic acids
with metal ion proceed to intermolecular free radical additions with 1,4-benzoquinone derivatives to obtain isopyrrole-1,4-benzoquinones.

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