Diepoxides vicinal

Reaction with Acetylenes. HOF MeCN reacts with most acetylenic compounds via the corresponding em-diepoxides (eqs 7 and 8). The products are similar to the ones obtained with other oxidants although the yields are usually much higher, the reaction times considerably shorter and the whole process takes place at room temperature. Internal acetylenes are usually oxidized to vicinal diketones while external ones lose a CO fragment forming aldehydes. ... 

Salomon, R.G., Basu, B., Roy, S., and Sharma, R.B. (1989) Total synthesis of (+)-spatol a stereospedfic construction of vicinal diepoxides from 2,3-epoxy-l,4-diols. Tetrahedron Lett., 30, 4621-4624. 

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