REIMER TIEMANN REACTION PDF

Reaction mechanism[ edit ] The mechanism of the Reimer-Tiemann reaction Chloroform 1 is deprotonated by a strong base normally hydroxide to form the chloroform carbanion 2 which will quickly alpha-eliminate to give dichlorocarbene 3 ; this is the principal reactive species. The hydroxide will also deprotonate the phenol 4 to give a negatively charged phenoxide 5. The negative charge is delocalised into the aromatic ring, making it far more nucleophilic. Nucleophilic attack of the dichlorocarbene gives an intermediate dichloromethyl substituted phenol 7. After basic hydrolysis, the desired product 9 is formed. This interaction favors selective ortho-formylation.

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The Journal of Organic Chemistry , 71 23 , Paula A. Gillen, and, Pui-Kai Li. Journal of Medicinal Chemistry , 40 26 , Zearalenone and Related Compounds. William T. Miller, David M. Trichloromethyllithium, an Electrophilic Reagent. Journal of the American Chemical Society , 86 10 , Louis D.

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