Azetidinone Antibiotics. 22. A Rearrangement of Oxoazetidinesulfinic Acids to Haloazetidinones

Article abstract of DOI:10.1021/jo00330a046

Treatment of the oxoazetidinesulfinic acid 3 with a positive halogen source gave trans and cis 4-haloazetidinones 5; the trans isomer of 5 are easily converted to oxazoline 6 by chromatography on silica gel, while the cis isomers are transformed into 6 by