An analysis of the 1H and 13C nuclear magnetic resonance spectra of 3-t-butylaminoacrolein and of glyoxal t-butylhydrazone

Abstract

1 H N.m.r. spectra have confirmed that 3-t-butylaminoacrolein exists as the E-s-E configuration in polar solvents, and as a mixture of Z-s-Z and E-s-E isomers in non-polar solvents. The spectra of glyoxal t-butylhydrazone are independent of solvent and are thought to indicate Z-s-E structure for this compound. The fully coupled 13C n.m.r. spectra of both compounds have been completely assigned using specifically labelled derivatives where necessary. The long-range 13C–1H coupling constants of 3-t-butylaminoacrolein are strongly dependent on the shape of the conjugated system.