Ozonolysis of vinyl chloride in methanol: a convenient entry to methoxymethylhydroperoxide and its chemistry
- 1 October 1983
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 61 (10) , 2385-2388
- https://doi.org/10.1139/v83-413
Abstract
Ozonolysis of vinyl chloride (7) in methanol at −78 °C afforded methoxymethylhydroperoxide (10) in high yield along with only trace amounts of methyl formate (14). The former (10) was converted into a mixture of methyl formate (14) as the major and dimethylformal (18) as the minor product by HCl-catalysis in methanol. Reduction of 10 with dimethylsulfide and subsequent treatment with HCl–methanol gave dimethylformal (18). Partial reduction of 10 with a deficient amount of triphenylphosphine gave formaldehyde hemiacetal (19) and methoxymethylhydroxymethylperoxide (20).Keywords
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