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Synthesis of Diferrocenebutyl Disulfide

Author: YangXiaoHong
Tutor: BianZhanXi
School: Inner Mongolia University
Course: Organic Chemistry
Keywords: 4-chlorobutylferrocen phase transfer catalyst sulfurated borohydride exchange resin diferrocenebutyl disulfide orthogonal experiments
CLC: O627.8
Type: Master's thesis
Year: 2009
Downloads: 75
Quote: 1
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Abstract


4-chlorobutylferrocene was synthesized via the reaction of Friedel-Crafts Acylation and reduction from ferrocene.Then the paper mainly described two methods for the synthesis of Diferrocenebutyl disulfide and investigated the optimal reaction conditions by orthogonal experiments.The first method:Diferrocenebutyl disulfide was synthesized based on the reaction of 4-chlorobutylferrocene and sodium disulfide in the presence of phase transfer catalyst（PTC）.Effect of PTC species,material mole ratio and reaction temperature on the reaction was investigated.The optimal reaction conditions obtained by orthogonal experiments are as follows:tetrabutylammonium bromide（TBAB） as PTC,chloroform-water as solvent with Na2S:S:FcCH2CH2CH2-CH2Cl=1.6:1:1,the isolated yield of diferrocenebutyl disulfide reach 91.7%.The reaction afforded diferrocenebutyl disulfide in good to excellent isolated yields in a short time and was carried out easily.The second method:Diferrocenebutyl disulfide was synthesized from 4-chlorobutylferrocene using sulfurated borohydride exchange resin（SBER）.Effect of reaction temperature,amount of borohydride exchange resin and material mole ratio on the reaction was investigated.The optimal reaction conditions obtained by orthogonal experiments are as follows:at 60℃,methanol as solvent with S:FcCH2CH2CH2CHzCl=1.8:1,the isolated yield of diferrocenebutyl disulfide reach 89.7%.The obvious advantages of heterogeneous reagent in terms of simple operation with the ease of work-up,recyclability of the resin and friendship to environment are noteworthy.The structure of diferrocenebutyl disulfide had been characterized by elemental analysis,IR、1HNMR.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Elements in organic compounds > Ⅷ of group elements, organic compounds
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