Synthesis and properties of 3-oxo-1, 2-diazetidinium ylides

EC Taylor, NF Haley, RJ Clemens

Index: Taylor,E.C.; Haley,N.F.; Clemens,R.J. Journal of the American Chemical Society, 1981 , vol. 103, p. 7743

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Citation Number: 39

Abstract

Abstract Treatment of a-chloroacylhydrazones of diary1 and certain aralkyl and dialkyl ketones with sodium hydride in anhydrous tetrahydrofuran gives 1-(disubstituted methylene)- 3-oxo-1, 2-diazetidinium inner salts (ylides). The reaction pathway involves formation of the hydrazone anion followed by intramolecular SN2 halide displacement (with complete inversion at the a carbon) by the spz imine nitrogen. These 1-(disubstituted methylene)-3- ...