Conclusive evidence of the trapping of primary ozonides.
[reaction: see text] Anomalous ozonolysis of strained bicyclic allylic alcohols yields alpha-hydroxymethyl ketones. The proposed mechanism involves an unusual trapping of the primary ozonide that undergoes a Grob-like fragmentation instead of dissociating into the Criegee intermediates.
Jung
M E
ME
Department of Chemistry and Biochemistry, University of California, Los Angeles 90095, USA. jung@chem.ucla.edu
Davidov
P
P
D000438:Alcohols / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D010126:Ozone / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000438:Alcohols; D001643:Bridged Bicyclo Compounds; D007659:Ketones; D010126:Ozone