Conclusions
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1.
Five- and seven-stage methods were developed for converting ubiquinone-9 and the dibenzyl ether of the corresponding hydroquinone to ubiquinone-10 by use of the Wittig reaction at the key stage; the overall yield was 2 and 17%, respectively.
-
2.
The use of a pressure of 10–14 kbar was proposed for the direct synthesis of 2-methyl(hept-2-en-6-yl)triphenylphosphonium bromide.
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Literature cited
L. M. Kogan, E. A. Obol'nikova, and G. I. Samokhvalov, Khim. Farm. Zh.,17, 410 (1983).
N. V. Tarasova, E. A. Obol'nikova, A. D. Gololobov, and G. I. Samokhvalov, Pat. 3965130 (USA), Chem. Abstr.,85, 121846u (1976).
S. Terao, K. Kato, M. Shiraishi, and H. Morimoto, J. Chem. Soc. Perkin Trans. 1, 1101 (1978).
A. B. Veselovskii, A. I. Kozhukhova, E. A. Obol'nikova, et al., Zh. Org. Khim.,18, 292 (1982).
E. E. Van Tamelen and T. J. Curphey, Tetrahedron Lett., 121 (1962).
A. I. Kozhukhova, E. A. Obol'nikova, T. M. Filippova, et al., Zh. Org. Khim.,20, 1683 (1984).
G. Ohloff and W. Giersch, Helv. Chim. Acta,63, 1589 (1980); T. Mandai, H. Yamaguchi, K. Nishikawa, et al., Tetrahedron Lett.,22, 763 (1981).
A. B. Veselovskii, A. M. Moiseenkov. V. M. Zhulin, et al., Inventor's Certificate No. 1133278 (1984). published in Byull. Izobret., No. 1, 96 (1985).
I. M. Zaks, B. S. Él'yanov, V. M. Zhulin, and A. M. Moiseenkov, Izv. Akad. Nauk SSSR, Ser. Khim., 1094 (1984).
W. G. Dauben, J. M. Gerdes, and R. A. Bunce, J. Org. Chem.,49, 4293 (1984).
J. Tanigawa, H. Kanamaru, A. Sonoda, and S.-J. Murahashi, J. Am. Chem. Soc.,99, 2361 (1977).
E. Breitmaier and W. Voelter,13C NMR Spectroscopy, Verlag Chemie, Weinhein (1974), p. 127.
G. A. Tolstikov, V. N. Odinokov, V. P. Akhunova, et al., Izv. Akad. Nauk SSSR, Ser. Khim., 887 (1978).
A. V. Lozanova, V. P. Gul'tyai, A. N. Karaseva, and A. M. Moiseenkov, Izv. Akad. Nauk SSSR, Ser. Khim., 1370 (1983).
K. Ohno, R. Nishiyama, and R. Nagase, Tetrahedron Lett., 4405 (1979).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2086–2091, September, 1987.
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Moiseenkov, A.M., Veselovskii, A.B., Filippova, T.M. et al. Conversion of ubiquinone-9 to ubiquinone-10 by use of the wittig reaction. Russ Chem Bull 36, 1937–1943 (1987). https://doi.org/10.1007/BF00958351
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DOI: https://doi.org/10.1007/BF00958351