Synthetic Utilization of the Double Bond Cleavage Reactions

22 SYNTHETIC UTILIZATION OF THE DOUBLE BOND CLEAVAGE REACTIONS 

Commercially available cyclooligomers, such as the butadiene dimer 473, can be easily transformed via partial ozonolysis into bifunctional derivatives such as 474. These derivatives, with a rigorously defined location and configuration of the double bond, serve as valuable precursors to the preparation of natural products such as pheromones. The selectivity of the monooxidation of these reactions is ensured by a careful metering of one equivalent of ozone.  

The discovery of skeletal rearrangements produced a dramatic impact on the development of structural theory in the first half of this century. Numerous theoretical and experimental studies were carried out to formulate a consistent mechanistical description of the observed non-trivial transformations. Because of these efforts, the course of rearrangements in a diverse structural context can be now accurately predicted, or, at the very least, well accounted for. Skeletal rearrangements are therefore no longer a mere challenging curiosity of organic chemistry, but a new set of powerful and reliable synthetic tools. °  

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