Synthesis and Structure of (E)-3-Phenylmethylene-2-oxetanone: Comments on the Stability of Methylene β-Lactones

Article abstract of DOI:10.1055/s-1990-27035

A route to stereospecifically (E)-substituted methylene-2-oxetanones is exemplified by the preparation of the phenyl derivative 4, whose structure has been confirmed by a single crystal X-ray structure determination.The relative stability of the parent compound, 3-methylene-2-oxetanone (5) has been compared with that of the well-known 4-methylene-2-oxetanone (6) (ketene dimer), by use of calculations involving Gaussian 82 programs.