Synthesis and properties of 1-alkyl-4-(dimethylamino) pyridinium bis(trifluomethylsulfonyl)imides

Monika Stasiewicz *, Katarzyna Materna – Institute of Chemical Technology and Engineering, Poznan University of Technology, Poznań, Poland; Małgorzata Graś , Grzegorz Lota – Institute of Chemistry and Technical Electrochemistry, Poznan University of Technology, Poznań, Poland
Please cite as: CHEMIK 2016, 70, 9, 533–540

4-Dimethylaminopyridine (DMAP) is a pyridine derivative used in the chemical synthesis as a nucleophilic catalyst for various reactions such as esterification [1], acylation [2], β-lactam synthesis [3] and many others. As it is a strong nucleophile, it easily undergoes quaternisation. 1-alkyl-4- (dimethylamino)pyridinium bromides are described in the literature for the entire homologue series C4, C8-C16, C20 and C22. Compounds with substituents from octyl to tetradecyl are water soluble and effectively reduce surface tension [4]. 1-alkyl-4-(dialkylamino)pyridinium halides were tested as catalysts for the phase transfer and obtained comparable or higher yields than for conventional catalysts (quaternary ammonium salts) [5]. Chloromethylalkyl ethers and sulfides react with DMAP producing pyridinium chlorides with biological activity against bacteria and fungi, and also anti-static properties [6]. Moreover, they can be used as alkoxymethylating agents of NH groups in azoles [7].

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