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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; in revised form: 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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.

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