ISSN:
1573-8353
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract Stereospecificity of the 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, Z 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 and an 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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00515247
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