Catalytic Hydrogenation in Organic Syntheses by Paul Nels Rylander

By Paul Nels Rylander

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Org. Chem. 37, 2989 (1972). , Nippon Kagaku KaishiNo. 8, p. 1527 (1972); Chem. Abs. 11, 128572v (1972). Maxwell, C. , U . S . Patent 3,522,192, July 28, 1970. Meyer, A. , Adickes, H. , Politzer, I. , M a l o n e , G. , Kovelesky, A. C , N o l e n , R. , and P o r t n o y , R. C , J. Org. Chem. 38, 36 (1973). Milas, Ν . , and Fies, D . , J. Am. Chem. Soc. 72, 4844 (1950). , and W e e d o n , B. C. , J. Chem. Soc. p. 3294 (1953). , Justus Liebigs Ann. Chem. 577, 181 (1952). , T o m i n a g a , M .

Some of the above points are illustrated by the results of hydrogénation of 2-methylcyclopentylidenecyclopentane (Table II). Classic theory would suggest that this molecule should be adsorbed on the catalyst in such a way as to afford mainly the ds-paraffin. However, Siegel and Cozort (1975) anticipated that repulsive interactions between the 2,2' and 5,5' ring positions 44 3. Hydrogénation of Olefins e TABLE I I CH CH 3 Catalyst 5% 5% 5% 5% a CH 3 3 % Cis Pt-on-C Pd-on-C Rh-on-C Ru-on-Al 0 23 13 13 45 45 (at 4 5 % completion) D a t a of Siegel a n d C o z o r t (1975).

Smith, R. , Daves, G. D . , a n d D a t e r m a n , G. , J. Org. Chem. 40, 1593 (1975). Sokol'skaya, A. M . , a n d Anisimova, Ν . , Vestn. Akad. Nauk Kaz. SSR 29(6), 37 (1973); Chem. Abstr. 79, 77959f (1973). Sokol'skaya, A. M . , Bosyakova, Ε. N . , Ryabinina, S. , a n d Sokol'skaya, D . , Zh. Fiz. Khim. 46(11), 2939 (1972); Chem. Abstr. 78, 57586k (1973). Sokol'skaya, A. M . , F a s m a n , A. , Shoshenkova, V. , L o k h m a t o v a , V. F . , a n d Sokol'skii, D . , Prom. Obraztsy, Tovarnye Znaki 50(27), 59 (1973); Chem.

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