✍ Scribed by R. Monnier; T. Toïa
No coin nor oath required. For personal study only.
Solid cycloc'ecyl $-toluenesulfonate decomposes spontaneously a t room temperature into $-toluenesulfonic acid and cis-cyclodecene. Pure cyclodecyl $-toluenesulfonate gives by acetolysis a mixture of 80% trans-and 20% cis-cyclodecene. The non-classical, transannular course of these eliminations has been investigated by using starting material labeled with lac. By systematic degradation of the cyclodecenes obtained it has been found that the amount of transannular hydride shifts in products of spontaneons decomposition differs considerably from that in products of acetolysis. These results explain the disturbing discrepancies observed in earlier experiments l) 2), in which partly decomposed cyclodecyl $-toluenesulfonate must have been used.
The characteristic features of the acetolysis of the cyclodecyl $-toluenesulfonate - the steric acceleration, the stereospecificity and the transannular course of the elimination -can be explained by conformational analysis based on the stable conformation of the cyclodecane ring as determined by X-ray analysis6).
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