Intramolecular Oxygen Transfer on the Ozonolysis of a Diphenylcyclopentene Derivative

✍ Scribed by Charles W. Jefford; John Boukouvalas; Danielle Jaggi; Shigeo Kohmoto; GéRald Bernardinelli

• Publisher: John Wiley and Sons
• Year: 1986
• Tongue: German
• Weight: 504 KB
• Volume: 69
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19860690422

✦ Synopsis

The ozonolysis of ci. ~-3,4a,7,7a-tetrahydro-3,3-dimethyl-6,7a-diphenyl~yclopenta[l,2-e][l,2,4]trioxine (1) in CH2C1, at -78" gave the secondary endo ozonide 2 (43 % yield) and an acetal 3 (27% yield) derived from 0insertion at the orthu position of the C(7a) phenyl substituent. Both structures were elucidated by X-ray. Repetition of the ozonolysis in MeOH/CH,Cl, 20: 3 at -78" also gave the same two products in 12 and 15% yields, repectively, together with the hemiperacetal4 (54% yield) formally derived from the secondary ozonide by addition of MeOH. ') *)

We thank 0. Kennurd, F.