Conclusions
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1.
The telomerization of isoprene with piperidine on PdCl2+Ph3P, (Ph3P)2PdCl2, Pd(OAc)2+2Ph3P, Pd-(acac)2+2Ph3P, and Pd(OAc)2+2P(OC6H4CH3-o)3 catalyst systems in methanol proceeds with low regioselectivity and the formation of a mixture of isomeric N-(dimethyloctadienyl)piperidines.
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2.
The telomerization of isoprene with diethylamine on PdCl2+Ph3P and Pd(OAc)2+2Ph3P catalyst systems in methanol gives four major telomer products: N-(2,6-dimethyl-2,7-octadienyl)-, N-(3,7-dimethyl-2,7-octadienyl)-, N-(3,6-dimethyl-2,7-octadienyl)-, and N-(2,7-dimethyl-2,7-octadienyl)diethylamines.
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3.
The telomerization of isoprene with piperidine on Pd(acac)2 or Pd(OAc)2+4(BuO)3P catalyst systems in acetonitrile gives three major telomer products: N-(2,6-dimethyl-2,7-octadienyl)-, N-(3,7-dimethyl-2,7-octadienyl)-, and N-(2,7-dimethyl-2, 7-octadienyl)piperidines.
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Literature cited
J. Berger, C. Duschek, and H. Reichel, J. Prakt. Chem.,315, 1077 (1973).
M. Hidai, H. Ichiwatari, H. Jagi, E. Tanaka, K. Onozawa, and J. Uchida, J. Chem. Soc., Chem, Commun., 170(1975).
L. I. Zakharkin and S. A. Babich, Izv. Akad. Nauk SSSR, Ser. Khim., 2099 (1976).
H. Jagi, E. Tanaka, H. Ischiwatari, M. Hidai, and J. Uchida, Synthesis, 334 (1977).
L. I. Zakharkin, S. A. Babich, and I. V. Pisareva, Izv. Akad. Nauk SSSR, Ser. Khim., 1616(1976).
K. Suga, S. Watanabe, and K. Hijikata, Austral. J. Chem.,24, 197 (1971).
L. I. Zakharkin, V. N. Medvedkov, and E. A. Petrushkina, Zh. Obshch. Khim.,52, 2118 (1982).
H. Green, G. Schooles, and F. G. A. Stone, J. Chem. Soc., Dalton Trans., 309 (1978).
M. Hidai, H. Mizuta, K. Hirai, and J. Uchida, Bull. Chem. Soc. Jpn.,53, 2091 (1980).
W. Keim and M. Röper, J. Org. Chem.,46, 3702 (1981).
G. Hueppi, G. Pyser, and W. De Silva, West German Pat. No. 2,459,129 (1975); Chem. Abstr.,83, P114–228z (1975).
K. Takabe, T. Katagari, and J. Tanaka, Chem. Lett., 1025 (1977).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 886–890, April, 1983.
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Zakharkin, L.I., Petrushkina, E.A. & Podvisotskaya, L.S. Telomerization of isoprene with piperidine on complex palladium catalysts. Russ Chem Bull 32, 805–809 (1983). https://doi.org/10.1007/BF00953482
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DOI: https://doi.org/10.1007/BF00953482