AbstractsChemistry

Pinacolyltrimethylammonium hydroxide has been found to yield on decomposition at both 30° in vacuo, and at 100- 1600, a single pure olefin, tert.-butylethylene. This is the first time the mechanism of Ingold and co-workers for such decompositions has been tested in a convincing way. The absence of rearranged products, and of saturated or cyclic hydrocarbons indicates unequivocally that the decomposition proceeds, not through free radical formation, but by expulsion of a proton, probably induced by preliminary hydrogen bonding, followed by rupture of the carbon-nitrogen bond. This same mechanism has been successfully extended to the decomposition of xanthate esters.