Zur Kenntnis des Kohlenstoffringes. 76. Mitteilung. Acetolyse und spontane Zersetzung des Cyclodecyl‐<i>p</i>‐toluolsulfonates

Abstract

Abstract Solid cyclodecyl p ‐toluenesulfonate decomposes spontaneously at room temperature into p ‐toluenesulfonic acid and cis ‐cyclodecene. Pure cyclodecyl p ‐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 14 C. 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, in which partly decomposed cyclodecyl p ‐toluenesulfonate must have been used.