Chemistry of dioxiranes. 4. Oxygen atom insertion into carbon-hydrogen bonds by dimethyldioxirane

RW Murray, R Jeyaraman, L Mohan

Index: Murray, Robert W.; Jeyaraman, Ramasubbu; Mohan, Lily Journal of the American Chemical Society, 1986 , vol. 108, # 9 p. 2470 - 2472

Full Text: HTML

Citation Number: 115

Abstract

3" solution in the precursor ketone, Le., acetone in the case of 1. We now wish to report that 1 inserts an 0 atom into carbonhydrogen bonds of hydrocarbons to give alcohols or products derived from further oxidation of the alcohols. Furthermore, using suitable substrates, we have shown that the insertion reaction occurs stereospecifically with retention and displays a primary kinetic isotope effect (kH/kD= 4.97). Some examples of the reaction are the ...