本論文共分三個部分，主要是利用過渡金屬催化或促進非環狀的烯炔類化合物進行環化反應。第一部份是以 Grubbs 教授所發展的釕金屬錯合物為催化劑，使對掌性二烯炔類化合物進行合環置換反應形成對掌性雙環醚類化合物，藉由乙烯氣體的通入，可減少氧原子對釕金屬產生螯合作用而降低其催化性，且利用取代基的不同，可選擇性的得到單一產物。而所得之雙環醚類結構是許多天然物的主要架構，故此催化反應可應用於天然物合成的研究上。
第二部份是利用鈷金屬錯合物促進順式環氧烯炔類化合物進行環化加成反應，形成三環內酯化合物。在此反應中，鈷金屬和環氧乙烷及炔基會先進行 [5+1] 的環化加成反應，形成六圓環的δ-內酯中間物，接著和烯基進行環化反應形成另外兩個環，並根據通入的氣體為二氧化碳或氮氣，形成含有環丁烷或環戊酮的三環內酯化合物。此種方法在合成複雜的多環分子上具有極高的應用價值。
第三部份是研究釕金屬錯合物 TpRu(PPh3)(CH3CN) 2PF6 催化烯二炔類進行芳香化反應，當炔基上接有長碳鏈時，碳-氫鍵會被活化而形成外接五圓環。而當我們以不同的親核性試劑如水、醇類、氨類等作為反應溶劑時，這些親核性試劑則會加成至芳香環上，並具有極高的位向選擇性，可應用於不同官能基芳香環衍生物的合成上。

Intramolecular cyclization of enynes mediated by organocobalt and ruthenium are discussed in this thesis. In the first chapter, we prepared a series of chiral 3,4-bisallyoxy-but-1-ynes having syn and anti configurations. Treatment of these substrates with Grubbs catalyst CL2(PCy3)2Ru=CHPh preferably gave chiral dioxabicyclo[4.4.0]- decane in addition to dioxabicyclo[5.3.0]decane in minor properties. On substitution of the 4-but-2-enyloxy group, the metathesis reactions produced only dioxabicyclo[5.3.0]decane in the presence of Grubbs ruthenium-imidazolidene carbine catalyst.
The second chapter discusses Co2(CO)8-mediated coupling of cis-epoxyalkyne, CO, and olefin functionalities, leading to tandem [5+1]/[2+2+1] and [5+1]/[2+2]-cycloaddition reactions to give tricyclic δ–lactones efficiently. The mechanism involves cyclocarbonylation to form δ–lactone intermediate, followed by oxidative cyclization to give cobalt-containing cyclopentane species. Insertion of CO or reductive elimination of this species leads to the derivative of cyclopentanone or cyclobutane products, respectively.
The third chapter describes TpRu(PPh3)(CH3CN) 2PF6 catalyzed aromatization of unfunctionalized endiynes. In the case of endiynes bearing a long alkyl substituent, the aromatization accompanied by a C-H bond insertion to form a cyclopentane ring. Highly nucleophilic addition of water, alcohols, aniline, acetylacetone, pyrroles and dimethyl malonate to endiynes gave functionalized benzene products in good yields. This method is very useful because it provides easy access to functionalized aromatic compounds from readily available unfunctionalized enediynes.

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