Chemistry of Heterocyclic Compounds p. 1104 - 1109 (1985)
Update date:2022-08-04
Topics:
Denisenko, S. N.
Shustov, G. V.
Chervin, I. I.
Kostyanovskii, R. G.
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-triazabicyclo<3.1.0>hexanes was observed.Proceeding from this, the preferred conformations of the d,l and meso isomers of 2,4,6-trialkyl-1,3,5-triazabicyclo<3.1.0>hexanes 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.
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