• Abstract
• Full-Text PDF [927 KB]
• Full-Text XML
• Article Versions Notes

• Article Statistics
• Google Scholar
• Order Reprints

• Cite this article
• Export to BibTeX
• Export to EndNote

• [+] on DOAJ
• Froschauer, C
• Weber, HK.
• Kahlenberg, V
• Laus, G
• Schottenberger, H
• [+] on Google Scholar
• Froschauer, C
• Weber, HK.
• Kahlenberg, V
• Laus, G
• Schottenberger, H
• [+] on PubMed
• Froschauer, C
• Weber, HK.
• Kahlenberg, V
• Laus, G
• Schottenberger, H

•  CiteULike
•  Facebook
•  Mendeley
•  Twitter

This article is

• freely available
• re-usable

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

Article

Iminium Salts by Meerwein Alkylation of Ehrlich’s Aldehyde

Carmen Froschauer ^1,2 , Hedda K. Weber ² , Volker Kahlenberg ³ , Gerhard Laus ^1,*  and Herwig Schottenberger ^1,*

¹ Faculty of Chemistry and Pharmacy, University of Innsbruck, 6020 Innsbruck, Austria ² Competence Centre of Wood Composites and Wood Chemistry K-Plus, Altenbergerstraße 69, 4021 Linz, Austria ³ 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

Download PDF Full-Text [927 KB, uploaded 18 March 2013 13:28 CET]

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

Article Statistics

Cite This Article