OXIDATIVE CLEAVAGE OF MONOSUBSTITUTED, DISUBSTITUTED, AND TRISUBSTITUTED OLEFINS TO METHYL-ESTERS THROUGH OZONOLYSIS IN METHANOLIC NAOH

The ozonolysis of alkenes in methanolic NaOH or NaOMe with CH2Cl2 as c osolvent leads directly to methyl esters. The procedure has been used to prepare various alpha-, beta, and omega-alkoxy esters, acyloxy este rs, and alpha- and beta-N-acyl and N-sulfonyl esters from the appropri ate unsaturated ethers, esters, and amides. Other examples include the formation of dimethyl octanedioate from cyclooctene (75% yield), dime thyl nonanedioate and methyl nonanoate from methyl oleate (77 and 78%, respectively), and tetradecanoic acid gamma-lactone from 2-methyl-2-h exadecen-6-ol (80% yield).