41807-89-0Relevant academic research and scientific papers
STEREOSPECIFITY OF 3JCH SPIN-SPIN COUPLING CONSTANTS IN BICYCLIC cis-DIAZIRINES: STEREOCHEMISTRY OF 2,4,6-TRIALKYL-1,3,5-TRIAZABICYCLOHEXANES
Denisenko, S. N.,Shustov, G. V.,Chervin, I. I.,Kostyanovskii, R. G.
, p. 1104 - 1109 (1985)
Stereospecifity of 3JC,N,C,H spin-spin coupling constants (3Jtrans > Jgauche) in the 13C NMR spectra of 1,5-diaza- and 1,3,5-triazabicyclohexanes was observed.Proceeding from this, the preferred conformations of the d,l and meso isomers of 2,4,6-trialkyl-1,3,5-triazabicyclohexanes were established, and a mechanism for the interconversion of these isomers via openings of the five-membered ring ans imino-enamine equilibrium was proposed.It is also shown, that the stereochemical result of the Schmitz reaction is determined in the step involving cyclization of the iminium intermediate.
