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Crystals 2013, 3(1), 248-256; doi:10.3390/cryst3010248
Article

Iminium Salts by Meerwein Alkylation of Ehrlich’s Aldehyde

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Received: 25 January 2013 / Revised: 6 March 2013 / Accepted: 11 March 2013 / Published: 18 March 2013
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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 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.

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