K. Hiratani, T. Nakai, M. Okawara
Nov 1, 1973
Citations
0
Influential Citations
8
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The reactions of (1,3-dithiolan-2-yl)trimethylammonium iodide (5), readily obtained by methylation of 2-dimethylamino-1,3-dithiolane (2), with aromatic amines were studied. It was found that 5 served as an electrophilic 1,3-dithiolanylating reagent; the reactions with aniline, N-methylaniline, and benzylamine gave N-dithiolanylated products while those with N,N-dimethylaniline and indole yielded exclusively C-dithiolanylated products via aromatic substitutions. Furthermore, C-dithiolanylated compounds were hydrolyzed to aldehydes using HgO–BF3·OEt2. The present aldehyde synthesis has been compared with an alternative electrophilic formylation method the Vilsmeier reaction.