Aryl Ethers from Arenediazonium Tetrafluoroborate Salts: from Neat Reactions to Solvent-mediated Effects

Authors

James A. Shriver, Central College
Daniel P. Flaherty, Central College
Cameron C. Herr, Central College

Document Type

Research

Keywords

synthesis, undergraduate research, benzenediazonium salts, aryl ether, aryl cation

Abstract

A general procedure for the synthesis of various aryl ethers via the thermal decomposition of benzenediazonium tetrafluoroborate salts is described. Studies performed in neat alcohol at 60°C gave aryl ethers in yields ranging from 0-73%. Upon completion of a series of reactions, the effect of solvent was explored to expand the scope and relevance of this procedure. It was found that even solvents that are traditionally non-nucleophilic gave rise to products including bi-aryls and N-aryl acetamides. The utilization of an ionic liquid, l-butyl-4-methylpyridinium tetrafluoroborate, resulted in yields comparable to reactions performed in neat alcoholic solvents.

Publication Date

January-December 2009

Journal Title

Journal of the Iowa Academy of Science

Volume

116

Issue

1-4

First Page

27

Last Page

35

Copyright

© Copyright 2010 by the Iowa Academy of Science, Inc.

Language

EN

File Format

application/pdf

Recommended Citation

Shriver, James A.; Flaherty, Daniel P.; and Herr, Cameron C. (2009) "Aryl Ethers from Arenediazonium Tetrafluoroborate Salts: from Neat Reactions to Solvent-mediated Effects," Journal of the Iowa Academy of Science: JIAS, 116(1-4), 27-35.
Available at: https://scholarworks.uni.edu/jias/vol116/iss1/6