OZONOLYSIS OF OLEFINS .8. SYNTHESIS OF PHENOXYACETALDEHYDES BY OZONOLYSIS OF ALLYLPHENYLETHERS

A new route for the preparation of a series of phenoxyacetaldehydes (2 a-j) which are useful intermediates or products, is described. It star ts from the easily available allylphenylethers 1a-j which are ozonized at - 40 degrees C and further treated with dimethylsulfide to give so lutions of the corresponding phenoxyacetaldehydes 2a-j; these are puri fied by column chromatography. Reaction of 2a-j with 1-methyl-1-phenyl hydrazine leads to the corresponding hydrazones 3a-c, 3e-g, 3i, and 3j . The aldehydes can also be transformed into the stable dimethylcetals 4a, 4e, 4h, and 4i by reaction with trimethyl orthoformate.