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[2+3]-Cycloadditions of Diazoalkanes with Imines of Hexafluoroacetone and Chloral

Mloston G., Bodzioch A., Cebulska Z., Linden A., Heimgartner H.

Polish Journal of Chemistry

2007

Vol. 81, nr 5-6

631-641

The reactions of N-arylimines 1 and 2 of hexafluoroacetone and chloral, respectively, with diazoalkanes at –60C to room temperature led to the corresponding 4,5-dihydro- 1H-[1,2,3]triazoles 4 and 5, in a regioselective [2+3]-cycloaddition. The structure of one example in each case has been established by X-ray crystallography. The thermal decomposition of these adducts yielded the corresponding aziridines, bearing two trifluoromethyl and one trichloromethyl group, respectively, at C(2).