Ozonolysis of 1-substituted 2,3-diphenylindenes and o-(1 -substituted-2-phenyl-3-methoxy-2-propenyl)benzophenones. Remarkable effects of the method of generation of the carbonyl oxide intermediates on the stereochemistries of both the ozonide and the methanol-derived isochroman products

Norinaga Nakamura, Tomohiro Fujisaka, Masatomo Nojima, Shigekazu Kusabayashi, Kevin J. McCullough

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Pages (from-to)1799-1803
Number of pages5
JournalJournal of the American Chemical Society
Volume111
Issue number5
Publication statusPublished - 1989

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