Iminium Salts by Meerwein Alkylation of Ehrlich’s Aldehyde
oleh: Gerhard Laus, Herwig Schottenberger, Volker Kahlenberg, Hedda K. Weber, Carmen Froschauer
| Format: | Article |
|---|---|
| Diterbitkan: | MDPI AG 2013-03-01 |
Deskripsi
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.