A general synthesis of 1-alkyl-4-vinylpyridinium ions. Alkylation of 4-vinylpyridine with primary alkyl triflates

WK Fife, P Ranganathan, M Zeldin

Index: Fife, Wilmer K.; Ranganathan, Prema; Zeldin, Martel Journal of Organic Chemistry, 1990 , vol. 55, # 21 p. 5610 - 5613

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Citation Number: 44

Abstract

1-Alkyl-4-vinylpyridinium trifluoromethanesulfonates, prepared by alkylation of 4- vinylpyridine with trifluoromethanesulfonate (triflate) esters of primary alcohols (ROTf) in dry dichloromethane at 0" C, are stable, storable salts. The protium, methyl, and dodecyl salts have been isolated as crystalline solids. The ethyl, butyl, and hexyl analogues are usually obtained as viscous liquids. All of these salts readily polymerize to the related poly (1-alkyl ...

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