R. R. Fraser, R. B. Swingle
1969
Citations
0
Influential Citations
15
Citations
Journal
Tetrahedron
Abstract
Abstract The reaction of trichloroacetyl chloride with triethylamine is found to produce a α-acylenamine by oxidation of the tertiary amine to diethylvinylamine, then acylation. Evidence is obtained which indicates that the enamine is formed by an elimination reaction of the initially formed addition complex, A slower reaction occurred with 1.4-diazabicyclo[2.2.2]octane but the product was shown to have resulted from a Von Braun type of ring opening. The NMR and IR spectra of the β-acylenamine provide evidence that it possesses a trans substituted double bond and an exclusive s-cis conformation.