Thermally induced opening of the diaziridine ring in 6-aryl-2-methyl-1,5-diazabicyclo[3.1.0]hexanes |
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Authors: | Yu B Koptelov S P Saik |
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Institution: | (1) St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia |
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Abstract: | Thermally induced opening of the diaziridine ring in 6-aryl-2-methyl-1,5-diazabicyclo3.1.0]-hexanes at the carbon-nitrogen bond is characterized by low regioselectivity; isomerization of unstable intermediate azomethine imines leads to mixtures of the corresponding 1-arylmethyl-5-methyl-4,5-dihydro-1H-pyrazoles and 1-arylmethyl-3-methyl-4,5-dihydro-1H-pyrazoles at a ratio of ~6:5. Analogous regioselectivity in opening of the three-membered ring is observed in the presence of phenyl isocyanate. In this case, adducts with cis arrangement of the aryl and methyl groups are formed as the major products (cis/trans ratio ~3:1). |
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