Ozonolysis of substituted 1,2-dichloroethylenes in methanol: products and reaction course

Abstract

TAE-SEONG HUH, JOACHIM NEUMEISTER, and KARL GRIESBAUM. Can. J. Chem. 59. 3188 (1981) Ozonolysis of trrins-2,3-dichloro-2-butene (5a). of trans-3.4-dichloro-3-hexene (5b), and of 1.2-dichlorocyclohexene in methanol and in solutions of sodium methoxide in methanol have been examined. They afforded in high yields the corresponding ester fragments methyl acetate (6a). methyl propionate (6b), and dimethyl adipate (a), respectively. By trapping with phenylacetylene and formation of 1.1-dichloro-2.2-dimethoxy-2-phenylethan the presence of methyl hypochlorite in the ozonolysis products was cstablishcd. A rcaction course has been proposed which is in accord with these results.

Ozonolysis of vinyl chloride in methanol: a convenient entry to methoxymethylhydroperoxide and its chemistry

“…The conceivable alternate mode of cleavage of 8 into fragments 11 and 12. on the other hand, occurs only to a very minor extent, at best. For, formaldehyde (1 1) or products dcrivcd from it like dimethylformal (18) or trimeric formaldeliyde were not detected, and methyl formate (14), the cntl product expected from the zwitterion fragment 12 by the sequence 12 + 13 + 14 (4). was only present in trace amounts.…”