Hermann Richtzenhain

Rubber. XVIII. Various Ozonides of Rubber and the Problem of the Existence of the Primary Ozonides of Harries

Abstract A permanently valuable service was rendered by Harries when he introduced the ozone cleavage of unsaturated compounds as a general method of investigation in organic chemistry. By analogy with other addition reactions of double bonded carbon atoms he derived the formula (a) for the ozonides which are first formed, but to support the existence of which he was able to obtain only scant experimental data. Harries relied above all on two observations, first, that mesityl oxide ozonide reverts to mesityl oxide when heated by itself, and, secondly, that fumaric acid is supposed to combine loosely with ozone and then readily split off again. Both of these suppositions have remained undisputed up to the present time. Harries reported that it was not possible, with any of a wide variety of reducing agents, to reduce the ozonides to the original compounds or to 1,2-glycols, as would be expected from their structure. Staudinger has laid great stress on this fundamental objection, and he considers that most ...