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

Full Text: HTML

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- ...

 Related Synthetic Route

~80%

~53%

~30%

~77%

~84%

~81%

~0%

~%

~59%

~72%

~57%

~%

~76%

~%

~%

~67%

~%

~%

~60%

~%

~73%

~%

~%

~66%

~93%

~81%

~90%

~81%

~%

~%