Preview

Kataliz v promyshlennosti

Advanced search
Open Access Open Access  Restricted Access Subscription or Fee Access

Dichloro-[2,2]-paracyclophane. Methods for Synthesis

https://doi.org/10.18412/1816-0387-2018-5-19-30

Abstract

Methods for synthesis of dichloro-[2,2]-paracyclophane (dichloroPCP) are discussed. DichloroPCP is a valuable monomer to prepare polymer coats for electronics. This monomer is not produced in Russia. Analysis of available synthetic techniques leads to conclude that the Hofmann method for cleavage of quaternary ammonium salts is the most appropriate for the industrial production. Application of catalytic technologies – alkali catalysis and catalysis by Lewis acids – is the promising way for practical implementation of this four-stage process.

About the Authors

L. L. Gogin
Boreskov Institute of Catalysis, Novosibirsk
Russian Federation


D. Yu. Yushchenko
Boreskov Institute of Catalysis, Novosibirsk
Russian Federation


V. N. Konev
Boreskov Institute of Catalysis, Novosibirsk
Russian Federation


E. E. Sergeev
Boreskov Institute of Catalysis, Novosibirsk
Russian Federation


E. G. Zhizhina
Boreskov Institute of Catalysis, Novosibirsk
Russian Federation


T. B. Khlebnikova
Boreskov Institute of Catalysis, Novosibirsk
Russian Federation


Z. P. Pai
Boreskov Institute of Catalysis, Novosibirsk
Russian Federation


References

1. Brown C.J., Farthing A.C. // Nature. 1949. V. 164. P. 915-916.

2. Paradies J. // Synthesis. 2001. V. 23. P. 3749-3766.

3. Пат. Китая 103613618, 2015.

4. David O.R.P. // Tetrahedron. 2012. V. 68. P. 8977-8993.

5. Gibson S.E., Knight J.D. // Org. Biomol. Chem. 2003. V. 1. P. 1256-1269.

6. Takenaga N., Adachi S., Furusawa A., Nakamura K., Suzuki N., Ohta Y., Komizy M., Mukai C., Kitagaki S. // Tetrahedron. 2016. V. 72. P. 6892-6897.

7. Bisai V., Singh V.K. // Tetrahedron Letters. 2016. V. 57. P. 4771-4784.

8. Hopf H., Gleiter R. (Eds.). Modern Cyclophane Chemistry. Weinheim: Wiley-VCH, 2004. P. 159.

9. De Meijere A., Konig B. // Synlett. 1997. V. 11. P. 1221-1232.

10. US Patent 3342754, 1967.

11. Hopf H. // Angew. Chem. Int. Ed. 2008. V. 47. P. 9808-9812.

12. Vogtle F., Neumann P. // Synthesis.1973. V. 2. P. 85-103.

13. US Patent 3149175, 1964.

14. US Patent 3247274, 1966.

15. US Patent 3258504, 1966.

16. US Patent 34400295, 1969.

17. Пат. РФ 2043323, 1992.

18. Шевелькова Л.В., Соколовская В.Г., Гусельников Л.Е. // Изв. вузов. Химия и химическая технология. 1993. Т. 36. № 7. С. 80—87.

19. Kawakami S., Iwaki S., Nakada M., Yamaguchi T. // Bull. Chem. Soc. Jpn. 1991. V. 64. P. 1000-1004.

20. US Patent 2013/0109827, 2013.

21. Kirk-Othmer Encyclopedia of chemical technology, 4th Ed, vol. 26, p. 430.

22. Кардаш И.Е. и др. Химия и применение поли-n-ксилиленов. В сб. Итоги науки и техники. М., 1984. Т. 19. C. 84.

23. Otsubo T., Mizogami S., Sakata Y., Misumi S. // Tetrahedron Letters. 1973. № 27. P. 2457-2460.

24. Pan D., Wang Y., Xiao G. // Beilstein J. Org. Chem. 2016. V. 12. P. 2443-2449.

25. GB Patent 807196, 1956.

26. US Patent 2757146, 1956.

27. US Patent 4675462, 1987.

28. Пат. Бразилии 8605269, 1987.

29. Winberg H.E., Fawcett F.S. // Org. Syntheses. 1962. V. 42. P. 83.

30. Chow H.-F., Low K.-H., Wong K.I. // Synlett. 2005. № 14. P. 2130-2134.

31. Кочетков Н.К. (Ред.). Общая органическая химия. М.: Химия, 1981. Т. 3. С. 68—70.

32. US Patent 4532369, 1985.

33. US Patent 4795838, 1989.

34. US Patent 4806702, 1989.

35. US Patent 4734533, 1988.

36. US Patent 4769505, 1987.

37. US Patent 4816608, 1989.

38. US Patent 4853488, 1989.

39. US Patent 5110903, 1992.

40. Пат. Японии 041146, 1992.

41. Wang Z.-J., Dong F.-X., Lu J. etc. // Chinese Journal of Organic Chemistry. 2001. V. 21. № 7. P. 538-540.

42. Tao N., Xiao G., Tong Y., Niu L. // Fine Chemicals. 2009. V. 26. № 12. P. 1159-1162.

43. Пат. Китая 105348029, 2015.

44. Long Z., Juan W., Leng G., Yulun X., Weimin G. // Proc. of SPIE. 2005. V. 6029. P. 1-6.

45. Пат. ЧССР 247592, 1998.

46. Пат. РФ 2101272, 1998.

47. US Patent 4783561, 1988.

48. US Patent 4849559, 1989.

49. US Patent 5679874, 1997.

50. Пат. Японии 074759, 1995.

51. Ito Y., Miyata S., Nakatsuka M., Saegusa T. // J. Org. Chem. 1981. V. 46. P. 1044-1045.

52. Cram D.J., Steinberg H. // J. Am. Chem. Soc. 1951. V. 73. P. 5691-5702.

53. Крам Д. // Успехи химии. 1960. Т. 29. С. 1029—1047.

54. Tacahashi S., Mori N. // Chem. Lett. 1989. V. 18. № 1. P. 13-14.

55. Brown G.W., Sonheimer F. // J. Am. Chem. Soc. 1967. V. 89. P. 7116-7117.

56. Kaplan M.L., Truesdale E.A. // Tetrahedron Letters. 1976. V. 41. P. 3665-3666.

57. Boekelheide V., Reingold I.D., Tuttle M. // J. Chem. Soc., Chem. Commun. 1973. P. 406-407.

58. Vogtle F., Fornell P., Lohr W. // Chem. Ind. 1979. P. 416.

59. Coray A.R. // Journal of Organometallic Chemistry. 1983. V. 243. P. 191-193.

60. Пат. Польши 162243, 1990.

61. Higuchi H., Kugimiya M., Otsubo T., Sakata Y., Misumi S. // Tetrahedron Letters. 1983. V. 24. № 25. P. 2593-2594.

62. Higuchi H., Tani K., Otsubo T., Sakata Y., Misumi S. // Bull. Soc. Chem. Jpn. 1987. V. 60. P. 4027-4036.

63. Higuchi H., Misumi S. // Tetrahedron Letters. 1982. V. 23. № 52. P. 5571-5574.

64. Higuchi H., Otsubo T., Ogura F., Yamaguchi H., Sakata Y., Misumi S. // Bull. Soc. Chem. Jpn. 1982. V. 55. P. 182-187.

65. Takemura H., Shinmyozub T., Inazu T. // Tetrahedron Letters. 1988. V. 29. № 9. P. 1031-1032.

66. Isaji H., Sako K., Takemura H., Tatemitsu H., Shinmyozi T. // Tetrahedron Letters. 1998. V. 39. P. 4303-4304.

67. Isaji H., Sako K., Yasutake M., Takemura H., Tatemitsu H., Inazu T., Shinmyozi T. // Eur. J. Org. Chem. 2001. P. 2487-2499.

68. Higuchi H., Misumi S. // Tetrahedron Letters. 1982. V. 23. P. 5335-5338.

69. Shinmyom T., Hirai Y., Inazu T. // J. Org. Chem. 1986. V. 51. P. 1551-1555.

70. Szunerits S., Utley J.H.P., Nielsen M.F. // J. Chem. Soc., Perkin Trans. 2000. V. 2. P. 669-675.

71. US Patent 3616314, 1971.

72. Hopf H. // Angew. Chem. Int. Ed. 1972. V. 11. № 5. P. 419-420.

73. US Patent 3221068, 1965.

74. Yeh V.L., Gorham W.F. // J. Org. Chem. 1969. V. 34. № 8. P. 2366-2370.

75. Reich H.J., Cram D.J. // J. Am. Chem. Soc. 1969. V. 91. P. 3527-3533.


Review

For citations:


Gogin L.L., Yushchenko D.Yu., Konev V.N., Sergeev E.E., Zhizhina E.G., Khlebnikova T.B., Pai Z.P. Dichloro-[2,2]-paracyclophane. Methods for Synthesis. Kataliz v promyshlennosti. 2018;18(5):19-30. (In Russ.) https://doi.org/10.18412/1816-0387-2018-5-19-30

Views: 696


ISSN 1816-0387 (Print)
ISSN 2413-6476 (Online)