728013-86-3Relevant academic research and scientific papers
Generation of azomethine imines via opening of the diaziridine ring in unsymmetrically substituted 6-aryl-1,5-diazabicyclo-[3.1.0]hexanes and their transformations
Koptelov, Yu. B.,Saik,Molchanov,Selivanov
, p. 421 - 432 (2011/06/23)
Thermally induced opening of the diaziridine ring at the carbon-nitrogen bond in unsymmetrically substituted 6-aryl-1,5-diazabicyclo[3.1.0]hexanes is characterized by low regioselectivity which is likely to be determined by the inductive effect of substituents in the trimethylene bridge. 1,3-Dipolar cycloaddition of the resulting azomethine imines to phenyl isocyanate is regioselective: it occurs at the double carbon-nitrogen bond with predominant formation of the corresponding cis adducts due to dipolarophile approach to Z-azomethine imine at the sterically less hindered side. Analogous approach of dipolarophile is also observed in the reaction with N-arylmaleimides.
