caa a22 4500 475759958 CHVBK 20180406123547.0 cr unu---uuuuu 170329e20001201xx s 000 0 eng 10.1023/A:1009580110623 doi (NATIONALLICENCE)springer-10.1023/A:1009580110623 Peculiarities of electroreduction of trans-2-allyl-6-methyl(allyl,phenyl)-1,2,3,6-tetrahydropyridines [Elektronische Daten] [L. Korotayeva, T. Rubinskaya, E. Klimkina, V. Gultyai, Yu. Bubnov] Electrochemical reduction of trans-2-allyl-6-R-1,2,3,6-tetrahydropyridines (R = Me, All, and Ph) on the mercury cathode in anhydrous DMF (with 0.1 M Bu4NClO4 as the supporting electrolyte) resulted in catalytic hydrogen evolution, while in the case of anhydrous DMF the electrochemical activity of the endocyclic double bond was dictated by the nature of the R substituent at the carbon atom neighboring the double bond. The electrocatalytic hydrogenation of the piperideines under study on the Ni (Nidisp/Ni) cathode in 40% aqueous DMF in the presence of a tenfold excess of AcOH yielded the corresponding trans-2-propyl-6-R1-piperidines (R1 = Me, Pr, and Ph). Using trans-2,6-diallyl-1,2,3,6-tetrahydropyridine as an example, the conditions (with annealed copper as the cathode) for selective hydrogenation of the double bonds in allyl substituents with preservation of the endocyclic double bond were found. Plenum Publishing Corporation, 2000 trans -2-allyl-6-methyl(allyl,phenyl)-1,2,3,6-tetrahydropyridine nationallicence cis - and trans -2-allyl-6-phenylpiperidine nationallicence trans -6-methyl(propyl,phenyl)-2-propyl-1,2,3,6-tetrahydropyridine nationallicence trans -6-propyl-2-methyl(propyl,phenyl)piperidine nationallicence electrocatalytic hydrogenation nationallicence electroreduction nationallicence Korotayeva L. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Rubinskaya T. E-mail: guvp@ioc.ac.ru aut Klimkina E. E-mail: guvp@ioc.ac.ru aut Gultyai V. E-mail: guvp@ioc.ac.ru aut Bubnov Yu A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/12(2000-12-01), 2037-2044 1066-5285 49:12<2037 2000 49 11172 https://doi.org/10.1023/A:1009580110623 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1023/A:1009580110623 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Korotayeva L. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Rubinskaya T. E-mail: guvp@ioc.ac.ru aut NATIONALLICENCE 700 1- Klimkina E. E-mail: guvp@ioc.ac.ru aut NATIONALLICENCE 700 1- Gultyai V. E-mail: guvp@ioc.ac.ru aut NATIONALLICENCE 700 1- Bubnov Yu A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut NATIONALLICENCE 773 0- Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/12(2000-12-01), 2037-2044 1066-5285 49:12<2037 2000 49 11172 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer