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I Attempted Friedel-Crafts Alkylation Under Neutral Conditions II Preliminary Studies On The New Synthesis Ofβ-Bromoethers

Posted on:2006-02-21Degree:MasterType:Thesis
Country:ChinaCandidate:J ZhangFull Text:PDF
GTID:2121360182475922Subject:Organic synthesis
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The first part of the dissertation was based on the attempted Friedel-Craftsalkylation under neutral conditions. The Friedel-Crafts alkylation was the mostpowerful carbon-carbon bond-forming processes in organic synthesis. The originalprocedure has subsequently been replaced by milder and more environmentallyfriendly conditions. We tried to alkylate 3,4,5-trimethoxytoluene by2-allylphenylbenzyl ether in the presence of N-bromosuccinimide.We got theexpected product as evidenced by the analysis of 1H-NMR, but in low yield .Weassumed that in the course of reaction there was benzyl cation produced, but benzylcation was very reactive group which could have reacted with other nucleophiles.In the second part of the dissertation, a new procedure for protecting alcohol asbromoether was preliminary studied. Hydroxyl groups are present in a number ofcompounds of biological and synthetic interest. Hydroxyl group must be protected insome of the alcohol reactions. Ethers are often used as protective groups.5-Mehtyl-5-hexenenitrile reacted with different alcohols in thr presence of 1 eq ofNBS, yielding corresponding bromoether as single products under mild conditions.According to the analysises of 1H-NMR spectra, 13C-NMR spectra, GC spectra, andIR spectra. It is reported that zinc could react with bromoether to yield alcohol in highyield. Therefore the method of synthesis ethers is a potential method to pretectalcohols.
Keywords/Search Tags:Friedel-Crafts alkylation, N-bromo-succinimide, 5-mehtyl-hex-5-enenitril
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