Advertisement

Polymerization and Other Organic Reactions in the Crystalline State

  • Herbert Morawetz

Abstract

Reactions of molecular crystals which do not involve polymerization may exhibit several features reflecting the crystalline order of the reagent, e.g., (a) anisotropy of reactions of the crystals with gases, (b) topotaxy, (c) selection of one of several possible reaction paths, (d) the formation of optically active reaction products from achiral or racemic reagents by the influence of a chiral crystal environment. Solid-state polymerizations are discussed particularly with respect to topotactic effects and the control of the reaction product by the geometric arrangement of monomer molecules in the monomer crystal. The survey deals with (a) the polymerization of trioxane, (b) the polymerization of crystals of vinyl monomers and their clathrate complexes, (c) the “polydimerization” of Ephenylene diacrylic acid derivatives and of distyrylpiperazine and (d) the preparation of large single polymer crystals by the homogeneous solid-state polymerization of diacetylene derivatives.

Keywords

Crystalline State Organic Reaction Vinyl Monomer Dioic Acid Cyclobutane Ring 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    C.N.R. Rao, “Solid State Chemistry”, Marcel Dekker, New York (1974).Google Scholar
  2. 2.
    H. Morawetz,in Physics and Chemistry of the Organic Solid State, D.Fox, M.M. Labes, A.Weissberger, eds., Interscience, New York, vol. 1(1963) pp. 287–328; vol.2(1965) pp. 853–872.Google Scholar
  3. 3.
    M.D. Cohen and B.S. Green, Chem.Brit., 9, 490 (1973).Google Scholar
  4. 4.
    I.C. Paul and D.Y.Curtin, Acc.Chem.Res., 6, 217 (1973).CrossRefGoogle Scholar
  5. 5.
    J.M. Thomas,Phil.Trans., A277, 251 (1974).CrossRefGoogle Scholar
  6. 6.
    I.C. Paul and D.Y. Curtin, Science, 187, 19 (1975).CrossRefGoogle Scholar
  7. 7.
    M.D. Cohen,Angew.Chem.,Internat.Ed., 14,386 (1975).Google Scholar
  8. 8.
    R.E. Pincock, K.R. Wilson and T.E. Kiovsky, J.Am. Chem. Soc., 89, 6890 (1967).CrossRefGoogle Scholar
  9. 9.
    R.E. Pincock, M.M. Tong and K.R. Wilson, J. Am. Chem. Soc., 93, 1669 (1971).CrossRefGoogle Scholar
  10. 10.
    J.D. McCullough, D.Y. Curtin and I.C. Paul, J. Am. Chem.Soc., 94. 874 (1972).CrossRefGoogle Scholar
  11. 11.
    F.W. Comer and J. Trotter, J. Chem.Soc., B, 11 (1966).Google Scholar
  12. 12.
    K. Lonsdale, E. Nave and J.F. Stephens, Phil. Trans., 261, 1 (1966).CrossRefGoogle Scholar
  13. 13.
    S.R. Byrn, D.Y. Curtin and I.C. Paul, J.Am.Chem. Soc., 94, 890 (1972).CrossRefGoogle Scholar
  14. 14.
    J.Z. Gougoutas and J.C. Clardy, Acta Crystal., B, 26, 1999 (1970).Google Scholar
  15. 15.
    J.Z. Gougoutas, Pure Appl.Chem., 27, 305 (1971).CrossRefGoogle Scholar
  16. 16.
    H. Morawetz, Science, 152, 705 (1966).CrossRefGoogle Scholar
  17. 17.
    K. Penzien and G.M.J. Schmidt, Angew. Chem., 81, 628 (1969).CrossRefGoogle Scholar
  18. 18.
    M.D. Cohen, in“Topochemistry and G.M.J. Schmidt”, Verlag Chemie, (1976).Google Scholar
  19. 19.
    G.M.J. Schmidt, J. Chem. Soc., 2014 (1964).Google Scholar
  20. 20.
    G.M.J. Schmidt, Pure Appl. Chem., 27, 647 (1971).CrossRefGoogle Scholar
  21. 21.
    M.D. Cohen, E. Elgavi, B.S. Green, Z. Ludmer and G.M.J. Schmidt, J.Am.Chem.Soc., 94, 6776 (1972).CrossRefGoogle Scholar
  22. 22.
    A. Elgavi, B.S. Green and G.M.J. Schmidt, J.Am. Chem. Soc., 95, 2058 (1973).CrossRefGoogle Scholar
  23. 23.
    G. Friedman, M. Lahav and G.M.J. Schmidt, J. Chem. Soc., Perkin Trans. II, 428 (1974).Google Scholar
  24. 24.
    K.R. Wilson and R.E. Pincock, J.Am.Chem.Soc., 97, 1474 (1975).CrossRefGoogle Scholar
  25. 25.
    M. Lahav, F. Laub,E. Gati, L. Leiserowitz and Z. Ludmer, J. Am. Chem. Soc., in press.Google Scholar
  26. 26.
    S. Okamura and K. Hayashi, Makromol. Chem., 47, 230, 237 (1961).Google Scholar
  27. 27.
    a) J. Lando, N. Morosoff, H. Morawetz and B. Post, J.Polymer Sci., 60 S24 (1962); (b) S. Okamura, K. Hayashi and M. Nishii, J.Polymer Sci., 60 S26 (1962).Google Scholar
  28. 28.
    G. Carrazzolo,’S. Leghissa and M.Mammi, Makromol. Chem., 60, 771 (1963).Google Scholar
  29. 29.
    H.B. van der Heijde and P.H.G. Kasteren, Phil.Mag., 13, 1039 (1966).CrossRefGoogle Scholar
  30. 30.
    H.B. van der Heijde, Phil.Mag., 13, 1055 (1966).CrossRefGoogle Scholar
  31. 31.
    A. Komaki and T. Matsumoto, Polymer Lett., 1, 671 (1963).CrossRefGoogle Scholar
  32. 32.
    J.P. Colson and D.H. Reneker, J.Appl.Phys., 41, 4296 (1970).CrossRefGoogle Scholar
  33. 33.
    G. Wegner, A. Munoz-Escalona and E. W. Fischer, Ber.Bumsenges, 74, 909 (1970).Google Scholar
  34. 34.
    J.B. Lando and V. Stannett, J. Polymer Sci., Pt. A, 3, 2369 (1965).Google Scholar
  35. 35.
    G. Carazzolo, M. Mammi and G. Valle, Makromol.Chem., 100, 295 (1967).CrossRefGoogle Scholar
  36. 36.
    J.E. Herz and V. Stannett, Polymer Lett., 4, 995 (1966).CrossRefGoogle Scholar
  37. 37.
    H. Morawetz, Pure Appl.Chem., 12, 201 (1966).CrossRefGoogle Scholar
  38. 38.
    J. H. O’Donnell, B. McGarvey and H. Morawetz, J.Am. Chem. Soc., 86, 2322 (1964).CrossRefGoogle Scholar
  39. 39.
    M. J. Bowden and J.H. O’Donnell, Macromolecules, 1, 499 (1968).CrossRefGoogle Scholar
  40. 40.
    M.J. Bowden, J.H.O’Donnell and R.D. Sothman, Macromolecules, 5, 269 (1972).CrossRefGoogle Scholar
  41. 41.
    S.Z. Jakabhazy, H. Morawetz and N. Morosoff, J. Polymer Sci., Pt. C, 4, 805 (1964).CrossRefGoogle Scholar
  42. 42.
    N. Morosoff, H. Morawetz and B. Post, J. Am. Chem. Soc., 87, 3035 (1965).CrossRefGoogle Scholar
  43. 43.
    D.M. White, J.Am.Chem.Soc., 82, 5678 (1960).CrossRefGoogle Scholar
  44. 44.
    S. Krimm, J.J. Shipman, V.L. Folt and A.R. Berens, Polymer Lett., 3, 275 (1965).CrossRefGoogle Scholar
  45. 45.
    M. Farina, G. Audisio and G. Natta, J. Am. Chem. Soc., 89, 5071 (1967).CrossRefGoogle Scholar
  46. 46.
    M. Fari a, U. Pedretti, M.T. Gramegna and G. Audisio, Macromolecules, 3, 481 (1970).CrossRefGoogle Scholar
  47. 47.
    M.Farina,G. Audisio and M.T. Gramegna, Macromolecules, 4, 265 (1971); 5, 617 (1972).Google Scholar
  48. 48.
    Y. Chatani, S. Nakatani and H. Tadokoro, Macromolecules, 3, 481 (1970).CrossRefGoogle Scholar
  49. 49.
    A. Colombo and G. Allegra, Macromolecules, 4, 579 (1971).CrossRefGoogle Scholar
  50. 50.
    F. Suzuki, Y. Suzuki, H. Nakanishi and M. Hasegawa, J. Polymer Sci., 7, 2319 (1969).Google Scholar
  51. 51.
    M. Hasegawa, Y. Suzuki, F. Suzuki and H. Nakanishi, J. Polymer Sci., 7, 743 (1969).CrossRefGoogle Scholar
  52. 52.
    H. Nakanishi, Y. Suzuki, F. Suzuki and M.Hasegawa, J. Polymer Sci., 7, 753 (1969).Google Scholar
  53. 53.
    T. Tamaki, Y. Suzuki and M. Hasegawa, Bull.Chem. Soc. Japan, 45, 1988 (1972).Google Scholar
  54. 54.
    H.Nakanzshi,F`.Nakanishi,Y.Suzuki and H.Hasegawa, J.Polym.Sci.,Polym.Chem.Ed., 11, 2501 (1973).Google Scholar
  55. 55.
    H. Nakanishi, M. Hasegawa and Y. Sasada,J.Polymer Sci., 10, 1537 (1972).Google Scholar
  56. 56.
    L. Addadi, M.D. Cohen and M. Lahav, J.Chem.Soc., Chem. Commun., 471 (1975).Google Scholar
  57. 57.
    G. Wegner, Makromol. Chem., 154, 35 (1971).CrossRefGoogle Scholar
  58. 58.
    G. Wegner, Polymer Lett., 9, 133 (1971).CrossRefGoogle Scholar
  59. 59.
    E. Hädicke, E.C. Mez, C. H. Krauch, G. Wegner and J. Kaiser, Angew.Chem., 83, 253 (1971).CrossRefGoogle Scholar
  60. 60.
    J. Kaiser, G. Wegner and B.W. Fischer, Kolloid.Z.Z.Polym., 250, 1158 (1972).CrossRefGoogle Scholar
  61. 61.
    A. J. Melveger and R. H. Baughman, J. Polymer Sci., Polymer Phys. Ed., 11, 603 (1973).Google Scholar
  62. 62.
    R. H. Baughman, J. Appl. Phys., 43, 4363 (1972).Google Scholar
  63. 63.
    R. H. Baughman, J. Polymer Sci., Pt. A-2, 12, 1511 (1974).Google Scholar
  64. 64.
    G. Treiber, K. Boehlke, A. Weitz and B. Wunderlich, J. Polymer Sci., Polym. Phys., 11, 1111 (1973).CrossRefGoogle Scholar
  65. 65.
    R. Iwamoto, R.C. Bopp and B. Wunderlich, J. Polym. Sci., Polym. Phys., 13, 1925 (1975).CrossRefGoogle Scholar
  66. 66.
    E.M. Macchi, N.Morosoff and H. Morawetz, J. Polym. Sci., Pt. A-1, 6, 2033 (1968).CrossRefGoogle Scholar
  67. 67.
    E. Macchi, J. Polym. Sci., Pt. A-1, 10, 45 (1972).Google Scholar
  68. 68.
    E. Macchi, Macromol. Chem., 165, 313 (1973).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1977

Authors and Affiliations

  • Herbert Morawetz
    • 1
  1. 1.Department of ChemistryPolytechnic Institute of New YorkBrooklynUSA

Personalised recommendations