Reaction of the ozonides with methanol in the presence of chlorosulphonic acid: selective cleavage of the C–O bond of the peroxide bridge

Abstract

The reaction of the 1,2,4-trioxolans (ozonides)(1) with methanol in the presence of chlorosulphonic acid gives good yields of products formed via the corresponding α-methoxy hydroperoxides. The order of reactivity of the ozonides, as estimated by periodic measurement of the n.m.r. spectra of a mixture of the ozonide and chloro-sulphonic acid in CD₃OD, is as follows: (1a), (1b) > (1c), (1d), (1e), (1f), (1g) > (1h).