Ozonolyses of but-2-yne 1 in the presence of added carbonyl compounds 3 afford α-oxo ozonides 4. Subsequent cycloadditions between ozonides 4 and cyclohexanone oxide 6, generated in situ by ozonolysis of O-methylcyclohexanone oxime, yield in turn α-diozonides 7 into which have been incorporated the carbon skeletons of all three substrates involved. Ozonolyses of acyloxy-substituted but-2-ynes 9 yield the corresponding bicyclic α-oxo ozonides 11 which subsequently participate in analogous cycloadditions with 6 to produce the corresponding α-diozonides 12. X-Ray crystallographic analysis of the crystalline diozonide 12a shows that it has been formed exclusively by exo-addition of 6 to 11a.
|Original language||English (US)|
|Number of pages||4|
|Journal||Journal of the Chemical Society - Perkin Transactions 1|
|State||Published - Jun 7 1997|
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