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Synthesis 1990; 1990(9): 855-856
DOI: 10.1055/s-1990-27035
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Synthesis and Structure of (E)-3-Phenylmethylene-2-oxetanone: Comments on the Stability of Methylene ß-Lactones

Eva M. Campi* , Kenneth Dyall, Gary Fallon, W. Roy Jackson, Patrick Perlmutter, Andrew J. Smallridge
  • *Department of Chemistry, Monash University, Clayton, Victoria 3168, Australia
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Publication Date:
17 September 2002 (online)

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A route to stereospecifically (E)-substituted methylene-2- oxetanones is exemplified by the preparation of the phenyl deriva- tive 4, whose structure has been confirmed by a single crystal X-ray structure determination. The relative stability of the parent com- pound, 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.