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Report | Regular issue | Vol 22, No. 5, 1984, pp.1121-1124
Published online, 1st January, 1970
DOI: 10.3987/R-1984-05-1121
1-Acyloxypyridinium Ion: The Reactive Intermediate in a Modified Reissert-Henze Reaction

Wlmer K. Fife* and Brett D. Boyer

*Department of Chemistry, Indiana-Purdue University, PO Box 647, Indianapolis, IN 46223, U.S.A.

Abstract

Cyanation of 3-X-1-dimethylaminocarbonyloxypyridinium ions with trimethylsilane-carbonitrile or cyanide ion gives 3-methyl-2-pyridinecarbonitrile (~90%) contaminated with 5-methyl-2-pyridinecarbonitrile (~10%) when X = -CH3, and approximately equal amounts of the 3- and 5-X derivatives when X = -COOCH3. These product mixtures are identical to those obtained with the corresponding pyridine 1-oxides and dimethylcarbamoyl chloride in a modified Reissert-Henze reaction.