381192-72-9Relevant academic research and scientific papers
Regioselectivity in the addition of 1,3-dipolarophiles to 6-aryl-1,5-diazabicyclo[3.1.0]hexanes
Molchanov,Sipkin,Koptelov,Kopf,Kostikov
, p. 67 - 78 (2004)
Thermolysis of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in the presence of 1,3-dipolarophiles having an unsymmetrically substituted double C=C bond (such as N-arylimides derived from 2-aryl-substituted maleic, citraconic, and itaconic acids, ethyl propynoate, aryl isocyanates, and aryl isothiocyanates) leads to formation of the corresponding 1,3-dipolar cycloaddition products. The reaction is regioselective, and in most cases only one regioisomer is obtained. The addition direction depends on the 1,3-dipolarophile structure, i.e., electronic and steric factors determining the most effective orbital interaction upon approach of the reagent to substrate.
