第一章
經由自由基加成反應，以烯烴與添普調控所單離出之苯胺基丁烯酮基質（(E)-4-(phenylamino)-4-((2,2,6,6-tetramethylpiperidin-1-yl)oxy) prop-3-en-1-substituted -2-one）在搭配0.03當量的樟腦磺酸、加熱至120°C的氮氣環境下進行加成，在此條件下，可得到高產率的苯基胺二酮形式的產物（2-substituted-3-oxo-N-phenylbutanamide）。
除此之外，本反應更可與前一步驟之分子內氧化反應進行一鍋化反應，產率也大多能夠維持有一定的水準（50%-70%）。
第二章
本章記錄利用無金屬催化的自由基加成環化反應來進行1-烯丙基-2-乙烯基苯與亞硝基苯的環化，利用亞硝基苯的自由基活性來促使1-烯丙基-2-乙烯基苯這種類型的雙烯化合物進行[2+2+2]的環化，建構出一系列氮氧雜環之結構產物2-苯基代-2,3,3a,4,9,9a-六氫萘並[2,3-d]異噁唑（2-phenyl-2,3,3a,4,9,9a-hexahydronaphtho[2,3-d]isoxazole），這種新的環加成反應是目前少數是使用烯烴來進行[2+2+2]合環反應的例子，而本篇討論之反應可以在不添加溶劑之氮氣環境下，加熱至120°C成功產生出理想產物。

PART 1
Here, we described the synthesis of 2-substituted-3-oxo-N-phenylbutanamide through an efficient radical addition reaction. Optimizing the condition for the radical addition of alkenes with (E)-4-(phenylamino)-4-((2,2,6,6-tetramethylpiperidin-1-yl)oxy) prop-3-en-1-substituted-2-one, and we have it best performed at 120 oC in toluene that described with moderate to good yields. The structures of products consist of diketone and N-phenylamide, which could be used for further applications such as providing starting materials for Mannich reaction to synthesize natural products.

PART 2

This part of the dissertation deals with a metal free [2+2+2] radical cycloaddition of 1-allyl-2-vinylbenzene derivatives and nitrosobenzenes constructing (1S,4S)-2-phenyl-2,3,4,5-tetrahydro-1H-4,1-(epoxymethano) benzo[c]azepine derivatives. The advantages of this new radical cycloaddition are based on the easily accessible substrates and the readily achievable condition. There are only few examples using alkene for [2+2+2] radical cycloaddition reactions so far, which highlighted the value of this research.

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