Ozonolysis of enol ethers: formation of 3-alkoxy-1, 2-dioxolanes by concerted addition of a carbonyl oxide to an enol ether

H Keul, RL Kuczkowski, HS Choi

Index: Keul, Helmut; Choi, Hyung-Soo; Kuczkowski, Robert L. Journal of Organic Chemistry, 1985 , vol. 50, # 18 p. 3365 - 3371

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Citation Number: 37

Abstract

The ozonolyses of methyl vinyl ether, ethyl vinyl ether, and ethyl isopropenyl ether were studied in a variety of solvents. Alkoxy-1, 2, 4-trioxolanes and alkoxy-1, 2-dioxolanes were the main products in pentane and ester solvents. These products arose from the carbonyl oxide (H, COO) produced upon ozonolysis undergoing 1, 3-cycloaddition reactions with esters and activated olefins (enol ethers). From additional trapping experiments, the ...