探討β胺醇之α碳上立體障礙與電子效應對苯炔誘導形成碳與碳雙鍵反應之影響;Steric and Electronic Effects around the α-Carbon on β-Amino Alcohols in the Benzyne-Induced Olefination

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题名:	探討β胺醇之α碳上立體障礙與電子效應對苯炔誘導形成碳與碳雙鍵反應之影響;Steric and Electronic Effects around the α-Carbon on β-Amino Alcohols in the Benzyne-Induced Olefination
作者:	張軒愷;Chang,Shiuan-kai
贡献者:	化學研究所
关键词:	雙鍵合成;carbon-carbon double bond
日期:	2012-07-26
上传时间:	2012-09-11 18:37:41 (UTC+8)
出版者:	國立中央大學
摘要:	由本實驗室所開發的烯類化合物之新型合成途徑：以β-amino alcohols作為起始物，在鹼性環境下加入二硫化碳進行合環反應，形成中間產物1,3-thiazolidine-2-thiones，再由氟化銫和2-(trimethylsilyl)phenyl trifluoromethanesulfonate生成的苯炔進行[3 + 2]加成反應，開環脫去副產物N-benzyl-2-imino-1,3-benzodithioles後，即可生成具有高度立體專一性之碳與碳雙鍵產物。羥基的位向、不同取代基、立體障礙、電子效應關係著二硫化碳進行分子內親核取代反應之反應性，進而影響生成1,3-thiazolidine-2-thione之產率。實驗室過去的初期研究，僅止於利用β-amino alcohol羥基之碳原子上為沒有取代基或是單取代苯基和甲基兩種基團進行此新型烯化反應，在此特別設計各式不同型態之β-amino alcohols以利增加此烯化反應的應用性與廣泛度，並探討各種效應對於反應之影響。　　本論文於β-amino alcohols連接羥基之碳原子上，置換上九種不同型態的官能基團，雙取代有雙甲基及雙苯甲基，單取代基有苯甲基、乙烯基、正戊烷基、異丙基、methoxyphenyl、chlorophenyl、及phenol官能基團，對此九種官能基團進行本實驗的雙鍵合成探討，並做出結論。　　A new, stereospecific olefin synthesis from β-Amino alcohols: β-Amino alcohols was treated with CS2 in acetonitrile to produce 1,3-thiazolidine-2-thiones. 1,3-Thiazolidine-2-thiones was then added to a solution of 2-(trimethylsilylphenyl) trifluoromethanesulfonate and CsF in acetonitrile at room temperature. This would make [3 + 2] cycloaddition to give olefin products, along with side product N-benzyl-2-imino-1,3-benzodithioles. There are various factors like stereospecificity, hinderance of substituents, and electronic repulsion effect the olefination reaction. 　　In the early stages of research, we carried out olefination reaction by use of no substitute and single substitute like phenyl and methyl groups. My research project focused on study of olefination pathway by use of different substituent groups. We used various functional groups like benzyl, vinyl, n-hexyl, isopropyl, methoxyphenyl, chlorophenyl, and phenol, which were attached to the α-carbon on β-amino alcohols.　　Finally in our laboratory we successfully synthesized eight olefin compounds by use of β-amino alcohols with various functional groups.　Overall yield of olefination products indicated benzyne-induced olefination applicable in the all no substitute and single substitute around the α-carbon on β-amino alcohols.
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