OZONOLYSIS OF VINYL ETHERS IN SOLUTION AND ON POLYETHYLENE

Ozonolyses of the vinyl ethers la-f in methanol afforded almost exclusively the corresponding a-methoxy hydroperoxides 4, suggesting the preferred formation of the carbonyl oxides 2. In aprotic solvents including methyl formate, the predominant modes of decay of the carbonyl oxides 2 were cyclodimerization, reduction, and rearrangement, yet no ozonide formation. By contrast, ozonolyses of la-f on polyethylene gave the α-methoxy-substituted ozonides 14 in fair yields. Ozonolyses of la-f in the presence of added carbonyl compounds 6 in methylene chloride or ether yielded the corresponding cross ozonides. Judged from the ozonide yields, the reactivities of the carbonyl compounds follow the sequence: (ClCH2)2C═O > C1CH2COCH3> (CH3)2C═0 and 2-CF3C6H4CHO > PhCHO. © 1990, American Chemical Society. All rights reserved.