By W G Frankenberg
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Extra resources for Advances in Catalysis and Related Subjects, Volume 9
N . , and Campbell, B. , Chem. 5151 (1943). 2. Farkas, A . , Trans. 33, 837 (1937). 3. , Trans. 30, 1164 (1934). 4 . Linstead, R. P . , Doering, W. , Davis, S . , and Whetstone, R. , J . Am. Chem. 64, 1948 (1942). 6. Balandin, A. physik. Chem. 289-316 (1924) ; Chem. Abstr. 23,2872 (1929). 6 . Beckett, C. , Pitzer, K . , and Spitzer, R. , J . Am. Chem. 69. 2188 (1947). 7. Signaigo, F. , and Cramer, P. , J . Am. Chem. 66,3326 (1933). 8 . Bailey, W. J . , Hewitt, J. J . , J. Am. Chem. Soc. 77, 357 (1955).
9. , Ph. D. dissertation, Department of Chemistry, University of Arkansas, 1956. To be available on microfilm from University Microfilms, Ann Arbor, Michigan. 10. Hammond, G. , and Nevitt, T. , J . Am. Chem. 76, 4121 (1954). If. Wallach, O . , Beschke, E. , Ann. 347, 337, 342, 345 (1906); 396, 264 (1913). 24 SAMUEL SIEGEL AND MORRIS DUNKEL 12. , Bull. S O C . chim. France 13, 222 (1946). 15. , Bull. S O C . chim. France 13, 219 (1946). 4. Rossini, F. , Pitzer, K. , Arnett, R. , Brown, R. , and Pimentel, G.
Compare Table I). 2. ) 30. The latter two catalysts were used with methanol as a diluent. 3. The ratio of isomers obtained from the hydrogenation of 2 ,4-dimethylcyclohexene catalyzed by PtOz in methanol is essentially the same at -52 as at 26". 111. DISCUSSION OF RESULTS 1 . The Hydrogenation of the Isomers of Dimethylcyclohexene a. Nonstereospecifi Processes. Each olefin (over platinum oxide in acetic acid) yields a mixture which is always richer in the cis isomer. The 20 SAMUEL SIEGEL A N D MORRIS D U N K E L contrary result reported by Mousseron and Granger (12) for the hydrogenation of 1,3- and 2,4-dimethylcyclohexenesis attributed to their failure to achieve a satisfactory separation of the cis- and trans-1 ,3-dimethylcyclohexanes.