Dry ozonation. Method for stereoselective hydroxylation of saturated compounds on silica gel Academic Article uri icon

abstract

  • Sir: Ozone reacts slowly with saturated hydrocarbons in- serting oxygen atoms into their CH bonds, resulting in al- cohols and ket0nes.l This insertion occurs preferentially at the tertiary carbon atoms, with a retention of configura- tion. In spite of its preparative potentialities this reaction has been rarely used until now. One of the factors limiting the use of ozone as reagent for hydroxylation of saturated hy- drocarbons is its low solubility in organic solvents. Even at low temperatures at which ozone forms stable solutions in saturated hydrocarbons and no reaction is observed, its sol- ubility is slight (-0.1-0.3% by weight at -78°).2 At higher temperatures necessary for reaction to proceed at reason- able rate, the solubility of 0 3 is even smaller, necessitating prolonged ozonation periods. Furthermore, the reactivity of ozone toward most of the organic solvents3 limits its practical use as a hydroxylation reagent only to neat hydrocarbons …

publication date

  • July 1, 1975