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Iminium Salts by Meerwein Alkylation of Ehrlich’s Aldehyde
Faculty of Chemistry and Pharmacy, University of Innsbruck, 6020 Innsbruck, Austria
Competence Centre of Wood Composites and Wood Chemistry K-Plus, Altenbergerstraße 69, 4021 Linz, Austria
Institute of Mineralogy and Petrography, University of Innsbruck, 6020 Innsbruck, Austria
* Authors to whom correspondence should be addressed.
Received: 25 January 2013; in revised form: 6 March 2013 / Accepted: 11 March 2013 / Published: 18 March 2013
Abstract: 4-(Dimethylamino)benzaldehyde is alkylated at the N atom by dialkyl sulfates, MeI, or Me3O BF4. In contrast, ethylation by Et3O BF4 occurs selectively at the O atom yielding a quinoid iminium ion. 4-(Diethylamino)benzaldehyde is alkylated only at O by either Et or Me oxonium reagent. The iminium salts are prone to hydrolysis giving the corresponding hydrotetrafluoroborates. Five crystal structures were determined.
Keywords: alkylation; Ehrlich’s aldehyde; iminium salt; quinoid; quinone
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Froschauer, C.; Weber, H.K.; Kahlenberg, V.; Laus, G.; Schottenberger, H. Iminium Salts by Meerwein Alkylation of Ehrlich’s Aldehyde. Crystals 2013, 3, 248-256.
Froschauer C, Weber HK, Kahlenberg V, Laus G, Schottenberger H. Iminium Salts by Meerwein Alkylation of Ehrlich’s Aldehyde. Crystals. 2013; 3(1):248-256.
Froschauer, Carmen; Weber, Hedda K.; Kahlenberg, Volker; Laus, Gerhard; Schottenberger, Herwig. 2013. "Iminium Salts by Meerwein Alkylation of Ehrlich’s Aldehyde." Crystals 3, no. 1: 248-256.