Synthesis and reactions of 3-alkoxy-2H-azirines


  • Dedicated to Prof. Th. J. de Boer on the occasion of his retirement from the Chair of Organic Chemistry at the University of Amsterdam.


3-Alkoxy-2H-azirines 4 have been prepared by treatment of enol ethers 6 with iodine azide followed by base-catalysed elimination of HI and thermolysis of the resulting vinyl azide 5. Azirines 4 readily undergo electrophilic additions, to yield products resulting from cleavage of either the N(1)-C(3) or the N(1)-C(2) bond. Reaction of 4 with trimethylsilyl cyanide yields highly functionalized aziridines 12. Thermolysis of 4 produces C-alkoxy-N-vinylmethanimines.