Ozonolyses of 1-substituted 2,3-diphenylindenes 1a,b and o-(1-substituted-2-phenyl-3-methoxy-2-propenyl)benzophenones 8a,b in methanol-methylene chloride at -70°C, which should proceed through common carbonyl oxide intermediates 11a,b, afforded stereoisomeric methoxy hydroperoxides, 6a,b and 9a,b, respectively. The ozonide stereochemistry was also affected by the method of generation of the carbonyl oxide intermediate 11a: ozonolyses of 1,2,3-triphenylindene (1a) in CCl4, CH3CN, CH3CO2H-CH2Cl2 and CF3CH2OH-CH2Cl2 gave predominantly the exo-ozonide 2a, whereas the endo isomer 3a was obtained exclusively from the ozonolysis of keto olefin 8a in CH3CO2H-CH2Cl2 and CF3CH2OH-CH2Cl2. Moreover, in the ozonolysis of the keto olefin 8a, protic solvents assisted ozonide formation; endo-ozonide 3a was certainly obtained in the ozonolysis in the protic solvents (around 25% yield). No ozonides were isolated, however, from ozonolysis reactions carried out in aprotic solvents, CCl4 and CH3CN. © 1989 American Chemical Society.
|Number of pages||5|
|Journal||Journal of the American Chemical Society|
|Publication status||Published - 1989|