synthesis, undergraduate research, benzenediazonium salts, aryl ether, aryl cation
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.
Journal of the Iowa Academy of Science
© 2010 by the Iowa Academy of Science, Inc.
Shriver, James A.; Flaherty, Daniel P.; and Herr, Cameron C.
"Aryl Ethers from Arenediazonium Tetrafluoroborate Salts: from Neat Reactions to Solvent-mediated Effects,"
The Journal of the Iowa Academy of Science: JIAS: Vol. 116:
, Article 6.
Available at: http://scholarworks.uni.edu/jias/vol116/iss1/6