Criegee, Rudolf

Criegee, R. Ber. Dtsch. Chem. Ges. 1931, 64, 260. Rudolf Criegee (1902—1975) was bom in DUsseldorf, Germany. He earned his Ph.D. at age 23 under K. Dimroth at Wurzburg. Criegee became a professor at Technical Institute at Karlsruhe in 1937, a chair in 1947. He was known for his modesty, mater-of-factness, and his breadth of interests. 

Rudolf Criegee worked for the doctorate with Dimroth at Wurzburg on the mechanism of diazo coupling, but the results were initially recorded only in his dissertation (1925). He then undertook a comprehensive investigation of the reaction of lead tetraacetate with olefins and aromatic hydrocarbons and in 1930 at the age of 28 presented the results in his first publication, a40-page nnu/en paper. The results were hardly commensurate with the effort and experimental skill evident from the paper. Cyclohexene reacted in part by addition of two acetoxyl groups, as noted by Dimroth, to give a mixture of cis and trans products (2), and in part by... 

The arrow formalism lets us map out the formation of the ozonide. The 7t bond of the alkene reacts with ozone to produce the five-membered ring. These primary ozonides are extremely difficult to handle, and it took great experimental skill on the part of Rudolf Criegee (1902-1975) and his co-workers at the University of Karlsruhe in Germany to isolate the ozonide produced in the reaction between ozone and frarar-di-fcrf-butylethylene. A concerted mechanism predicts that the stereochemical relationship of the alkyl groups in the original alkene will be preserved in the ozonide, and this is what happens (Fig. 10.51). 

---