Perbenzoic aoid

The synthesis of epoxy ethers by peroxy acid treatment of suitable vinylic ethers, on the other hand, is complicated by the acid sensitivity of epoxy ethers. For example, Bergmann and Mk>keley1Ss claimed in 1921 to have prepared 1 -ethoxy-1 (2 -epoxyethane by the oxidation of ethyl vinyl ether with perbenzoic aoid, bat B years later modified their structure to a dioxone type of dimer.186 In 1 B0 Mous-seron and co-wcrkere1168-1184 reported the preparation of an epoxy ether from 1 -ethoxy-1 -eydohexene, but 4 years later Stevens and Taznma164 showed the compound obtained in this oxidation, not to have the structure initially assigned to it. 

Although Paul and Tohelitoheff1808 demonstrated in 1947 that 2,3-dihydropyran did not yield the desired epoxy ether with perbenzoic acid, Hurd and Edwards843 claimed in 1949 to have obtained Hus elusive subatanoe. More recently, however, Barker and oo-workers78 reported once again the failure of perbenzoic aoid to produce an epoxy ether from. 2,3-dihydropyran, and Wood and Fletcher confirmed this observation in the sugar Beries.lfi7s... 

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