Collect. Czech. Chem. Commun. 1996, 61, 1637-1641

Convenient Preparation of 1,3-Bis(dimethylamino)trimethinium Perchlorate, Tetrafluoroborate and Hexafluorophosphate

Zdeněk Arnolda, Dalimil Dvořákb and Miroslav Havránekb

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic
b Department of Organic Chemistry, Prague Institute of Chemical Technology,166 28 Prague 6, Czech Republic


Formylation of ethyl vinyl ether with (chloromethylene)dimethylammonium chloride prepared from dimethylformamide and oxalyl chloride or phosgene followed by successive treatment with dimethylamine and 70% perchloric acid leads to 1,3-bis(dimethylamino)trimethinium perchlorate 1a in high yield. Similarly, work-up of the reaction mixture after formylation with hexafluorophosphoric acid or dimethylamine tetrafluoroborate afforded 1,3-bis(dimethylamino)trimethinium hexafluorophosphate 1b or tetrafluoroborate 1c, respectively.

Keywords: Formylation; Trimethinium salts.