Oxidative cleavage of mono-, di-, and trisubstituted olefins to methyl esters through ozonolysis in methanolic sodium hydroxide
作者:James A. Marshall、Albert W. Garofalo
DOI:10.1021/jo00066a019
日期:1993.7
The ozonolysis of alkenes in methanolic NaOH or NaOMe with CH2Cl2 as cosolvent leads directly to methyl esters. The procedure has been used to prepare various alpha-, beta, and omega-alkoxy esters, acyloxy esters, and alpha- and beta-N-acyl and N-sulfonyl esters from the appropriate unsaturated ethers, esters, and amides. Other examples include the formation of dimethyl octanedioate from cyclooctene (75% yield), dimethyl nonanedioate and methyl nonanoate from methyl oleate (77 and 78%, respectively), and tetradecanoic acid gamma-lactone from 2-methyl-2-hexadecen-6-ol (80% yield).