Ozonolysis of 1-methylindenes. Solvent, temperature, and substituent electronic effects on the ozonide exo/endo ratio

…, T Fujisaka, M Nojima, S Kusabayashi…

Index: Miura, Masahiro; Fujisaka, Tomohiro; Nojima, Masatomo; Kusabayashi, Shigekazu; McCullough, Kevin J. Journal of Organic Chemistry, 1985 , vol. 50, # 9 p. 1504 - 1509

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Citation Number: 5

Abstract

Results (I) Ozonolysis in Aprotic Solvents. The ozonolysis of 1-methyl-3-phenylindene (IC) in hexane, carbon tetrachloride, methylene chloride, acetone, and acetonitrile at 20" C gave, in each case, a mixture of exo ozonide 2c and the endo isomer 3c in isolated yields of around 60%, the (1)(a) Osaka University.(b) Heriot-Watt University.(2) Miura, M.; Nojima, M.; Kusabayashi, S.; McCullough, KJ J. Am.