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Synthesis of New Plant Growth Regulators, Isomeric 1-(Dimethyloctyl)- and 1-Alkylpiperidinium and -morpholinium Halides by Telomerization of Isoprene with Secondary Amines

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Abstract

The known plant growth regulator, Al'den [1-(3,7-dimethyloctyl)-1-allylpiperidinium bromide], and also 1-(3,7-dimethyloctyl)-1-methylpiperidinium iodide were synthesized by treatment with allyl bromide and methyl iodide, respectively, of exhaustively hydrogenated 1-nerylpiperidine which was obtained by anionic telomerization of isoprene with piperidine. Various quaternary ammonium salts having a terpene sub- stituent with unnatural dimethyloctane skeleton, which effectively stimulate florification of Aster Chinensis L., were prepared by the action of alkyl halides on telomerization products derived from isoprene and piperidine or morpholine in the presence of palladium complexes.

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REFERENCES

  1. Terek, O.I. and Kalinovich, N.A., Dokl. Akad. Nauk USSR, Ser. B: Geol., Khim. Biol. Nauki, 1990, no. 2, p. 74.

  2. Prusakova, L.D. and Chizhova, S.I., Khimicheskaya regulyatsiya protsessov zhiznedeyatel'nosti rastenii (Chemical Regulation of Vital Activity of Plants), Yaroslavl: Yarosl. Gos. Univ., 1985, p. 60.

    Google Scholar 

  3. Kur'yata, V.G., Berestetskii, V.A., and Negretskii, V.A., Fiziol. Biokhim. Kul't. Rast., 1991, vol. 23, no. 6, p. 563.

    Google Scholar 

  4. Kur'yata, V.G., Dabizhuk, T.M., Remenyuk, G.L., Berestetskii, V.A., and Negretskii, V.A., Fiziol. Biokhim. Kul't. Rast., 1995, vol. 27, nos. 5-6, p. 374.

    Google Scholar 

  5. Zayed, E.A., El-Zawily, A.I., and Ibrahim, S.A., Angew. Botanic, 1985, vol. 59, p. 199.

    Google Scholar 

  6. Muromtsev, G.S., Pavlova, Z.N., Krasnopol'-skaya, L.M., and Nagubnova, L.I., Izv. Akad. Nauk SSSR, Ser. Biol., 1989, no. 1, p. 116.

  7. Muromtsev, G.S., Krasnopol'skaya, L.M., and Nagubnova, L.I., Dokl. Ross. Akad. Nauk, 1994, vol. 335, no. 3, p. 385.

    Google Scholar 

  8. Foerster, W. and Becker, H., Z. Naturforsch., Teil C, 1987, vol. 42, nos. 1-2, p. 33.

    Google Scholar 

  9. Haruta, H., Yagi, H., Iwata, T., and Tamura, S., Agric. Biol. Chem., 1974, vol. 38, no. 1, p. 141.

    Google Scholar 

  10. Reinbol'd, A.M., Morar', G.V., Pasechnik, G.S., and Popa, D.P., Khim. Prirodn. Soedin., 1990, no. 3, p. 338.

  11. FRG Patent no. 2 459 129, 1975; Chem. Abstr., 1975, vol. 83, no. 114 228 z.

  12. Hueppi, G.F., Bocion, P.F., and De Silva, W.H., Experientia, 1976, vol. 32, no. 1, p. 37.

    Google Scholar 

  13. Menhenett, R., Ann. Bot., 1979, vol. 43, no. 3, p. 305.

    Google Scholar 

  14. Knypl, J.S., Experientia, 1977, vol. 33, no. 6, p. 725.

    Google Scholar 

  15. Zakharkin, L.I., Petrushkina, E.A., Aksenova, N.P., Konstantinova, T.N., and Bavrina, T.V., Dokl. Ross. Akad. Nauk, 2001, vol. 379, no. 3, p. 402.

    Google Scholar 

  16. Takabe, K., Yamada, T., Katagiri, T., and Tanaka, J., Org. Synth., 1989, vol. 67, p. 48.

    Google Scholar 

  17. Takabe, K., Katagiri, T., and Tanaka, J., Bull. Chem. Soc. Jpn., 1973, vol. 46, p. 222.

    Google Scholar 

  18. Zakharkin, L.I., Guseva, V.V., and Petrushkina, E.A., USSR Inventor's Certificate no. 1 027 161, 1982; Byull. Izobret., 1983, no. 25, p. 87.

  19. Petrushkina, E.A. and Bregadze, V.I., Metalloorg. Khim., 1992, vol. 5, no. 5, p. 1161.

    Google Scholar 

  20. Zakharkin, L.I., Petrushkina, E.A., and Podvisotskaya, L.S., Izv. Akad. Nauk SSSR, Ser. Khim., 1983, no. 4, p. 886.

    Google Scholar 

  21. Zakharkin, L.I., Petrushkina, E.A., Chailakhyan, M.Kh., Aksenova, N.P., Konstantinova, T.N., and Bavrina, T.V., USSR Inventor's Certificate no. 1 415 709, 1984; Byull. Izobret., 2000, no. 8.

  22. Postnikov, V.A., Kakuliya, Ts.V., Khananashvili, L.M., Isaev, Yu.V., and Novikov, Yu.N., Izv. Akad. Nauk SSSR, Ser. Khim., 1979, no. 3, p. 671.

  23. Green, M., Scholes, G., and Stone, F.G.A., J. Chem. Soc., Dalton Trans., 1978, no. 4, p. 309.

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  1. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia

    E. A. Petrushkina & L. I. Zakharkin†

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  1. E. A. Petrushkina
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  2. L. I. Zakharkin†
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Petrushkina, E.A., Zakharkin†, L.I. Synthesis of New Plant Growth Regulators, Isomeric 1-(Dimethyloctyl)- and 1-Alkylpiperidinium and -morpholinium Halides by Telomerization of Isoprene with Secondary Amines. Russian Journal of General Chemistry 73, 1653–1657 (2003). https://doi.org/10.1023/B:RUGC.0000016041.29564.e9

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  • DOI: https://doi.org/10.1023/B:RUGC.0000016041.29564.e9

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