Etherification of Phenols by Amines via Transient Diazonium Intermediates
CANADIAN JOURNAL OF CHEMISTRY(2020)
Abstract
In this paper, the synthesis of alkyl aryl ethers from electron poor phenols and amines, using 1,3-propanedinitrite, is described. Due to the mild conditions, functionalized primary, secondary, and tertiary alkyl groups were successfully introduced, denoting a highly tolerant process that allows for unprotected alcohols and acetals. The reaction is thought to proceed through the formation of a diazonium intermediate that undergoes subsequent S(N)2 or S(N)1 reactions.
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Key words
diazotization,nitrite,ether,amine,synthesis
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