AZETIDINYL KETONE CHEMISTRY . C-METHYLATION REACTIONS AND STEREOSTRUCTURE - SPECTRA RELATIONSHIPS

The C‐methylation of the potassium salt of 1‐t‐butyl‐2‐phenyl‐3‐(p‐phenylbenzoyl)azetidine (1a) with methyl iodide was studied in three solvents, and the stereochemical outcome of the reaction was shown to be dependent upon the solvent used. These results are rationalized in terms of the probable relative rates of the reaction in the various solvents and/or the effect of solvent on the structure of the anionic intermediate. Similar treatment of the potassium salt of 1‐t‐butyl‐2‐phenyl‐3‐benzoylazetidine (3a) in ethyl ether gave a comparable result. The configurations of the epimeric C‐methyl products (2a and 2b, and 4a) were assigned on the basis of their spectral properties. With the aid of spectral data for a model compound, l‐t‐butyl‐3‐benzoyl‐azetidine (5), several stereostructure‐spectra relationships for 3‐azetidinyl ketones are presented. Copyright © 1969 Journal of Heterocyclic Chemistry