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Reakcje asymetrycznego otwierania pierścienia azyrydyn

Prusinowska N.

Wiadomości Chemiczne

2013

[Z] 67, 5-6

585--618

Aziridines, the nitrogenous analogues of epoxides, are useful building blocks for the synthesis of various functional materials and biologically active compounds. The reactivity of aziridines toward ring opening and expansion is dependent upon their extremely strained ring structures. Among the procedures of ring opening of aziridines, a nucleophilic ring-opening reaction is one of the major routes to highly functionalized compounds (Scheme 2). This short review focused on essentiac asymmetric ring opening reactions of aziridines including enantioselective ring opening of meso-aziridines and kinetic resolution of racemic aziridines with various hetero and carbon nucleophiles towards the synthesis of highly enantiomerically enriched 1,2-difunctionalized fine chemicals.

[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).