SHORT PATH SYNTHESES OF ALPHA-DIOZONIDES BY SEQUENTIAL OZONOLYSES OF ACETYLENES AND O-METHYL OXIMES

Ozonolyses of but-2-yen 1 in the presence of added carbonyl compounds 3 afford alpha-oxo ozonides 4. Subsequent cycloadditions between ozoni des 4 and cyclohexanone oxide 6, generated in situ by ozonolysis of O- methylcyclohexanone oxime, yield in turn alpha-diozonides 7 into which have been incorporated the carbon skeletons of all three substrates i nvolved, Ozonolyses of acyloxy-substituted but-2-ynes 9 yield the corr esponding bicyclic alpha-oxo ozonides Il which subsequently participat e in analogous cycloadditions with 6 to produce the corresponding alph a-diozonides 12. X-Ray crystallographic analysis of the crystalline di ozonide 12a shows that it has been formed exclusively by exo-addition of 6 to 11a.