Etherification of Phenols by Amines via Transient Diazonium Intermediates

CANADIAN JOURNAL OF CHEMISTRY(2020)

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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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