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研究生： 黃彬峰
Huang Ping Feng
論文名稱： 有機過渡金屬鐵、鉻羰基錯合物的合成及其在有機合成上的應用
The synthesis and application of transition metal iron and chromium carbonyl complexes
指導教授： 葉名倉
Yeh, Ming-Chang
學位類別： 碩士
Master
系所名稱： 化學系
Department of Chemistry
論文出版年： 2000
畢業學年度： 88
語文別： 中文
論文頁數： 158
中文關鍵詞： 鐵鉻羰基錯合物
英文關鍵詞： iron and chromium carbonyl complex
論文種類： 學術論文
相關次數： 點閱：122  下載：0 
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    • 1.(η7-環庚三烯基)三羰鉻陽離子錯鹽，與有機鋅銅試劑反應，生成7-exo-取代的（η6-環庚三烯）三羰鉻陽離子錯合物，但當（η6-環庚三烯）三羰鉻錯合物之環庚三烯有取代基時（methyl），即非常不穩定、易分解。
    2.(η5-環己雙烯)三羰鐵陽離子錯鹽，與有機鋅銅試劑反應，生成5-官能化烷鏈之（η4-環己雙烯）三羰鐵錯合物，以NOBF4進行配位基置換，若雙烯上支鏈為含胺基烷鏈時，一方面因配位基NO使鐵錯合物不穩定，另一方面胺基與酸（COOH）不同之性質，致使含胺基烷鏈之鐵錯合物無法進行分子內環化反應得環化產物。
    3.以樟腦酮菘酸為光學輔助基的環己雙烯衍生物與鐵錯合時，由於樟腦酮菘酸之立體效應與其上的酮基之導引作用，使鐵由特定方位進入而與雙烯錯合，得到1 個非鏡像異構物，將此三羰鐵錯合物以三苯碳陽離子移除氫陰離子，形成陽離子錯鹽，與鋅銅試劑反應，在-78℃下，可得官能化烷基取代之三羰鐵錯合物，再經水解，去錯合，可得optical pure的環己烯酮衍生物。

    1. Reaction of (η7- tropylium) tricarbonylchromium tetrafloroborate with functionalized zinc-copper reagent gives 7-exo-substituted adduct of (η6- cycloheptatriene) tricarbonylchromium complex . Hydride abstraction of (η6- cycloheptatriene) tricarbonylchromium complex , bearing methyl group in cycloheptatriene , using Ph3CBF4 led to cation of (η7- methyl tropylium) tricarbonylchromium tetrafloroborate salt , and unfortunately it was very un- stable , easy to oxidize to decompose by oxygen of air .
    2. Addition of specially functionalized zinc-copper reagent to (η5- cyclohexa- dienyl) tricarbonyliron cation salt afforded (η4- cyclohexadiene) iron complex with functionalized side chain of amino alkyl group at C-5 position. Treatment of the adduct with NOBF4，followed by Et3N at 0℃ failed to get intramolecular cyclization products. Because of ligand transformation by NO+ that produced more unstable iron cation, and the feature of amino group different from carboxylic group, it is failed to proceed intramolecular cyclization.
    3. The complexation reaction of the 1,3-cyclohexadiene derivatives bearing the ketopinic acid derivatives as chiral auxiliary with Fe2(CO)9 led only one diastereomer because of the direct effect of keto group of chiral auxiliary and stereo effect of bucky group of chiral auxiliary occupied special orientation. Removing hydride of (η4-cyclohexadiene)tricarbonyliron complex bearing the ketopinic acid derivatives as chiral auxiliary by trityl cation led (η5- cyclohexadienyl)tricarbonyliron cation salts. Reaction of this iron cation salts with functionalized zinc-copper reagent produced corresponding substituted (η4- cyclohexadiene)tricarbonyliron complex, and got the optical pure cyclo -hexenone derivatives after hydrolysis and decomplexation.

    目錄 中文摘要 英文摘要 第一章 緒論：…………………………………………………… 1 第二章 環庚三烯鉻羰基錯合物與帶官能基鋅銅試劑之親核性加成反應………………………………………………… 41 2.1 前言：……………………………………………………………….. 41 2.2 結果與討論：……………………………………………………….. 47 2.2.1 1-methylcycloheptatriene 2-50之合成：……………………... 47 2.2.2 帶官能基鋅銅試劑2-60之製備：…………………………… 49 2.2.3 Tricarbony[η7-methyltropylium]chromium tetrafloroborate 2-62之合成……………………………………………………………. 50 第三章 具胺基或醯胺基雙烯三羰鐵錯合物的分子內親核性加成反應－以四氟硼酸亞硝醯為媒介，合成含氮雙環化合物 3.1 前言：………………………………………………………………. 54 3.2 結果與討論：……………………………………………………….. 58 3.2.1 （η5-環己二烯）三羰鐵陽離子錯鹽的合成………………. 58 3.2.2 帶官能基鋅銅試劑的製備 …………………………………. 58 3.2.3 Tricarbonyl{N-3-exo-[(1-4-η)-1,3-cyclohexadienyl-5-yl] propylphthalimide} iron complex 3-35之合成 …………… 59 3.2.4 Tricarbonyl{3-exo-[(1-4-η)-cyclohexadienyl-5-yl]propylamine} iron complex 3-37之合成……………………………………… 60 3.2.5 Tricarbonyl{ N-substituted-3-exo-[(1-4-η)-cyclohexadienyl-5-yl] propylamine}iron complex 3-38、3-39之合成 …………. 61 3.2.6 分子內環化反應 ………………………………………….. 62 第四章 以樟腦酮菘酸為光學輔助基之三羰鐵錯合物為媒介，合成具掌性之環己烯酮衍生物 4.1前言：……………………………………………………………. 65 4.2 結果與討論…………………………………………………….. 73 4.2.1 R- ( 1,3-cyclohexadienyl-2-yl) Ketopinate 4-64之合成… 73 4.2.2 Tricarbonyl{R-[(1S,2S,3R,4R-η)- 1,3-cyclohexadienyl-2-yl] ketopinate }iron complex 4-66之合成 ………………… 74 4.2.3 帶有芐基鋅銅試劑4-74的合成 ……………………… 76 4.2.4 Tricarbonyl{R- [(1S,2R,3R,4R,6S)-6-benzyl-(1-4-η)-1,3- cyclo -hexadienyl-1-yl] ketopinate}iron complex 4-76 之合成 76 4.2.5 6S-benzyl-2-cyclohexen-l-one 4-79之合成：………… 78 4.3 結論： ………………………………………………………. 80 第五章 實驗部分 5.1 分析儀器及基本實驗操作 ………………………………… 81 5.2 實驗與光譜數據 …………………………………………… 83 5.2.1 Tricarbonyl{N-3-exo-[(1-4-η)-1,3-cyclohexadienyl-5-yl] propyl phthalimide}iron complex 3-35之合成 …………….. 83 5.2.2 Tricarbonyl{N-(o-hydroxymethylbenzoyl)-3-exo-[(1-4-η)-1,3- cyclohexadienyl-5-yl]propylamine}iron complex 3-36之合成.. 85 5.2.3 Tricarbonyl{3-exo-[(1-4-η)-1,3-cyclohexadienyl-5-yl]propyl amine}iron complex 3-37之合成 …………………… 87 5.2.4 Tricarbonyl{N-3-exo-[(1-4-η)-1,3-cyclohexadienyl-5-yl]propyl acetamide}iron complex 3-38之合成 ……………… 88 5.2.5 Tricarbonyl{N-(p-tolylsulfonyl)-3-exo-[(1-4-η)-1,3-cyclohexa -dienyl- 5-yl]propylamine}iron complex 3-39之合成 .. 90 5.2.6 R-(1,3-cyclohexadienyl-2-yl)ketopinate 4-64之合成 .. 91 5.2.7 Tricarbonyl{R-[(1S,2S,3R,4R-η)-1,3-cyclohexadienyl-2-yl] ketopinate} iron complex 4-66之合成 ……………….. 93 5.2.8 Tricarbonyl{R-[(1S,2S,3R,4R,5R-η)-1,3-cyclohexadienyl-2-yl] ketopinate} iron tetrafloroborate salt 4-75之合成 …… 106 5.2.9 Tricarbonyl{R-[(1S,2R,3R,4R,6S)-6-benzyl-(1-4-η)-1,3-cyclohexa -dienyl-1-yl] ketopinate} iron complex 4-76之合成 … 106 5.2.10 Tricarbonyl{ 6S-benzyl-(1-4-η)-1,3-cyclohexadien-1-ol}iron complex 4-78之合成 ………………………………… 121 5.2.11 6S-benzyl-2-cyclohexen-1-one 4-79之合成 ………. 121 第六章 參考文獻 123 附錄 錯合物3-35的1H NMR光譜 130 錯合物3-35的13C NMR光譜 131 錯合物3-35的H-H COSY 光譜 132 錯合物3-35的C-H COSY 光譜 133 錯合物3-36的1H NMR光譜 134 錯合物3-36的13C NMR光譜 135 錯合物3-36的H-H COSY 光譜 136 錯合物3-36的C-H COSY 光譜 137 錯合物3-37的1H NMR光譜 138 錯合物3-37的13C NMR光譜 139 錯合物3-37的C-H COSY 光譜 140 錯合物3-38的1H NMR光譜 141 錯合物3-38的13C NMR光譜 142 錯合物3-38的H-H COSY 光譜 143 錯合物3-38的C-H COSY 光譜 144 錯合物3-39的1H NMR光譜 145 錯合物3-39的13C NMR光譜 146 錯合物3-39的H-H COSY 光譜 147 錯合物3-39的C-H COSY 光譜 148 錯合物4-64的1H NMR光譜 149 錯合物4-64的13C NMR光譜 150 錯合物4-66的1H NMR光譜 151 錯合物4-66的13C NMR光譜 152 錯合物4-66的H-H COSY 光譜 153 錯合物4-66的C-H COSY 光譜 154 錯合物4-76的1H NMR光譜 155 錯合物4-76的13C NMR光譜 156 錯合物4-79的1H NMR光譜 157 錯合物4-79的13C NMR光譜 158

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