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The Sythsis And Application Of Chrial Trithiocarbonates Substituted By Menthyl And The Study Of Polymerzation

Posted on:2010-10-19Degree:MasterType:Thesis
Country:ChinaCandidate:Z ZhangFull Text:PDF
GTID:2231360302956441Subject:Organic Chemistry
Abstract/Summary:
Reversible Addition Fragmentation chain Transfer (RAFT) radical polymerization has got much attention since its discovery by Rizzardo and workers in 1998. It has become a powerful technique for the synthesis of well-defined polymers or copolymers with both low polydispersity and functionalized end group. Nowadays the reaseach for asymmetric radical polymerization has been drawing attention because of their wide range of potential applications. Nevertheless asymmetric reversible addition fragmentation chain transfer(RAFT) polymerization was not reported until now. Preparation of chiral RAFT reagents and applied to asymmetric RAFT polymerization had great future. Five kinds of chiral trithiocarbonates had been prepared and three of them had been tried to be applied in radical polymerization of TrMA, PDBSMA and TrMEO.In this article, five kinds of chiral trithiocarbonates had been highly stereoselective formed by neomenthanethiol reacted with CS2 and then reacted with L-menthyl bromide, ethyl bromide, (2S,35)-2-bromo-3-methylpentanoic acid and (2S,3S)-ethyl-2,3-dimethyl-pentanoate, (lR,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-bromopropanoate through Sn2 mechanism.Furthermore, three kinds of the chrial trithiocarbonates had been applied in polymerization of TrMA, PDBSMA and TrMEO.
Keywords/Search Tags:menthyl, trithiocarbonates, RAFT reagent, asymmetric radical polymerization, chrial synthsis
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