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Poly(substituted Methylene) Synthesis: Construction of C–C Main Chain from One Carbon Unit

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Polymer Materials

Part of the book series: Advances in Polymer Science ((POLYMER,volume 231))

Abstract

This review describes recent progress in the preparation of C–C main chain polymers, where the main chain is constructed from one carbon unit. The first example for this strategy is polymerization of diazoalkanes and aryldiazomethanes, which were extensively explored in the period 1950–1970, despite the high explosiveness of the monomers. The metal surface-catalyzed polymerization of diazoalkanes has recently attracted much attention, as an efficient method for coating the surface with nanometer-scale polymethylene thin films, which can be regarded as a useful substitute for polyethylene films. Diazocarbonyl compounds such as diazoacetates, diazoketones, and diazoacetamides with a variety of substituents have been polymerized by Pd-complexes to give poly(substituted methylene)s with polar functional groups. Rh(diene) complexes polymerize ethyl diazoacetate in a stereospecific manner, giving high molecular weight polymers (M n up to 270,000). Organoborane-initiated living polymerization of sulfoxonium methylides is remarkably effective as a method for preparing polymethylenes with a controlled chain length and a well-defined polymer architecture. Some polymerizations related to the above examples are also described.

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References

  1. Drent E, van Dijk R, van Ginkel R, van Oort B, Pugh RI (2002) Chem Commun 744

    Google Scholar 

  2. Luo S, Vela J, Lief GR, Jordan RF (2007) J Am Chem Soc 129:8946

    Article  CAS  Google Scholar 

  3. Kochi T, Noda S, Yoshimura K, Nozaki K (2007) J Am Chem Soc 129:8948

    Article  CAS  Google Scholar 

  4. Weng W, Shen Z, Jordan RF (2007) J Am Chem Soc 129:15450

    Article  CAS  Google Scholar 

  5. Chen C, Luo S, Jordan RF (2008) J Am Chem Soc 130:12892

    Article  CAS  Google Scholar 

  6. Guironnet D, Roesle P, Rünzi T, Göttker-Schnetmann I, Mecking S (2009) J Am Chem Soc 131:422

    Article  CAS  Google Scholar 

  7. Shea KJ (2000) Chem Eur J 6:1113

    Article  CAS  Google Scholar 

  8. Noels AF (2007) Angew Chem Int Ed 46:1208

    Article  CAS  Google Scholar 

  9. Bawn CEH, Ledwith A (1970) Encyc Polym Sci Technol 10:337

    Google Scholar 

  10. Cowell GW, Ledwith A (1970) Quart Rev 24:119

    Article  CAS  Google Scholar 

  11. Imoto M, Nakaya T (1972) J Macromol Sci Revs Macromol Chem C7:1

    Article  Google Scholar 

  12. Suginome M, Ito Y (2004) Adv Polym Sci 171:77

    Article  CAS  Google Scholar 

  13. Kantor SW, Osthoff RC (1953) J Am Chem Soc 75:931

    Article  CAS  Google Scholar 

  14. Feltzin J, Restaino AJ, Mesrobian RB (1955) J Am Chem Soc 77:206

    Article  CAS  Google Scholar 

  15. Davies AG, Hare DG, Khan OR, Sikora J (1963) J Chem Soc 4461

    Google Scholar 

  16. Bawn GEH, Ledwith A, Matthies P (1959) J Polym Sci 34:93

    Article  CAS  Google Scholar 

  17. Mucha M, Wunderlich B (1974) J Polym Sci 12:1993

    CAS  Google Scholar 

  18. Goubean J, Rohwedder KH (1957) Justus Liebigs Ann Chem 604:168

    Article  Google Scholar 

  19. Wada N, Morisaki Y, Chujo Y (2009) Macromolecules 42:1439

    Article  CAS  Google Scholar 

  20. Mango FD, Dvoretzky I (1966) J Am Chem Soc 88:1654

    Article  CAS  Google Scholar 

  21. Werner H, Richards JH (1968) J Am Chem Soc 90:4976

    Article  CAS  Google Scholar 

  22. Saini G, Campi E, Parodi S (1957) Gazz Chim Ital 87:342

    CAS  Google Scholar 

  23. Saini G, Nasini AG (1955–1956) Atti Accad Sci Torino 90:586

    Google Scholar 

  24. Redwith A (1956) Chem Ind 1310

    Google Scholar 

  25. Nasini AG, Trossarelli L, Saini G (1961) Makromol Chem 44/46:550

    Article  Google Scholar 

  26. Seshadri K, Atre SV, Tao YT, Lee MT, Allara DL (1997) J Am Chem Soc 119:4698

    Article  CAS  Google Scholar 

  27. Tao YT, Pandian K, Lee WC (1998) Langmuir 14:6158

    Article  CAS  Google Scholar 

  28. Guo W, Jennings GK (2002) Langmuir 18:3123

    Article  CAS  Google Scholar 

  29. Guo W, Jennings GK (2003) Adv Mater 15:588

    Article  CAS  Google Scholar 

  30. Bai D, Jennings GK (2005) J Am Chem Soc 127:3048

    Article  CAS  Google Scholar 

  31. Bai D, Habersberger BM, Jennings GK (2005) J Am Chem Soc 127:16486

    Article  CAS  Google Scholar 

  32. Bai D, Elliott SM, Jennings GK (2006) Langmuir 18:5167

    CAS  Google Scholar 

  33. Bai D, Hardwick CL, Berron BJ, Jennings GK (2007) J Phys Chem B 111:11400

    Article  CAS  Google Scholar 

  34. Bai D, Ibrahim Z, Jennings GK (2007) J Phys Chem C 111:461

    Article  CAS  Google Scholar 

  35. Doyle MP, Mckervey MA, Ye T (1998) Modern catalytic methods for organic synthesis with diazo compounds. Wiley-Interscience, New York

    Google Scholar 

  36. Zhang Z, Wang J (2008) Tetrahedron 64:6577

    Article  CAS  Google Scholar 

  37. Liu L, Song Y, Li H (2002) Polym Int 51:1047

    Article  CAS  Google Scholar 

  38. Ihara E, Haida N, Iio M, Inoue K (2003) Macromolecules 36:36

    Article  CAS  Google Scholar 

  39. Toyoda N, Yoshida M, Otsu T (1983) Polym J 15:255

    Article  CAS  Google Scholar 

  40. Ihara E, Ishiguro Y, Yoshida N, Hiraren T, Itoh T, Inoue K (2009) Macromolecules 42:8608

    Article  CAS  Google Scholar 

  41. Takahashi H, Itoh T, Ihara E, Inoue K (2009) Polym Prepr Jpn 58:2221

    Google Scholar 

  42. Asano T, Itoh T, Ihara E, Inoue K (2009) Polym Prepr Jpn 58:2220

    Google Scholar 

  43. Ihara E, Fujioka M, Haida N, Itoh T, Inoue K (2005) Macromolecules 38:2101

    Article  CAS  Google Scholar 

  44. Ihara E, Kida M, Fujioka M, Haida N, Itoh T, Inoue K (2007) J Polym Sci Part A Polym Chem 45:1536

    Article  CAS  Google Scholar 

  45. Ihara E, Hiraren T, Itoh T, Inoue K (2008) J Polym Sci Part A Polym Chem 46:1638

    Article  CAS  Google Scholar 

  46. Ihara E, Hiraren T, Itoh T, Inoue K (2008) Polym J 40:1094

    Article  CAS  Google Scholar 

  47. Oyama T, Fukui T, Naka K, Chujo Y (1999) Polym Bull 43:183

    Article  CAS  Google Scholar 

  48. Ihara E, Goto Y, Itoh T, Inoue K (2009) Polym J 41:1117

    Article  CAS  Google Scholar 

  49. Hetterscheid DGH, Hendriksen C, Dzik WI, Smits JMM, van Eck ERH, Rowan AE, Busico V, Vacatello M, Castelli VVA, Segre A, Jellema E, Bloemberg TG, de Bruin B (2006) J Am Chem Soc 128:9746

    Article  CAS  Google Scholar 

  50. Jellema E, Budzelaar PHM, Reek JNH, de Bruin B (2007) J Am Chem Soc 129:11631

    Article  CAS  Google Scholar 

  51. Rubio M, Jellema E, Siegler MA, Spek AL, Reek JNH, de Bruin B (2009) Dalton Trans 8970

    Google Scholar 

  52. Hooz J, Linke S (1968) J Am Chem Soc 90:6891

    Article  CAS  Google Scholar 

  53. Hooz J, Gunn DM (1969) Tetrahedron Lett 10:3455

    Article  Google Scholar 

  54. Pasto DJ, Wojtkwski PW (1970) Tetrahedron Lett 11:215

    Article  Google Scholar 

  55. Bai J, Burke LD, Shea KJ (2007) J Am Chem Soc 129:4981

    Article  CAS  Google Scholar 

  56. Ihara E, Kida M, Itoh T, Inoue K (2007) J Polym Sci Part A Polym Chem 45:5209

    Article  CAS  Google Scholar 

  57. Ihara E, Nakada A, Itoh T, Inoue K (2006) Macromolecules 39:6440

    Article  CAS  Google Scholar 

  58. Nishida H, Itoh T, Ihara E, Inoue K (2008) Polym Prepr Jpn 57:405

    Google Scholar 

  59. Shea KJ, Walker JW, Zhu H, Paz M, Greaves J (1997) J Am Chem Soc 119:9049

    Article  CAS  Google Scholar 

  60. Tufariello JJ, Lee LTC (1966) J Am Chem Soc 88:4757

    Article  CAS  Google Scholar 

  61. Tufariello JJ, Wojtkowski P, Lee LTC (1967) J Chem Soc Chem Commun 88:505

    Google Scholar 

  62. Tufariello JJ, Lee LTC, Wojtkowski P (1967) J Am Chem Soc 89:6804

    Article  CAS  Google Scholar 

  63. Busch BB, Paz MM, Shea KJ, Staiger CL, Stoddard JM, Walker JR, Zhou XZ, Zhu H (2002) J Am Chem Soc 124:3636

    Article  CAS  Google Scholar 

  64. Stoddard JM, Shea KJ (2003) Organometallics 22:1124

    Article  CAS  Google Scholar 

  65. Wagner CE, Rodriguez AA, Shea KJ (2005) Macromolecules 38:7286

    Article  CAS  Google Scholar 

  66. Busch BB, Staiger CL, Stoddard JM, Shea KJ (2002) Macromolecules 35:8330

    Article  CAS  Google Scholar 

  67. Zhou XZ, Shea KJ (2000) J Am Chem Soc 122:11515

    Article  CAS  Google Scholar 

  68. Sulc R, Zhou XZ, Shea KJ (2006) Macromolecules 39:4948

    Article  CAS  Google Scholar 

  69. Bai J, Shea KJ (2006) Macromol Rapid Commun 27:1223

    Article  CAS  Google Scholar 

  70. Shea KJ, Lee SY, Busch BB (1998) J Org Chem 63:5746

    Article  CAS  Google Scholar 

  71. Shea KJ, Busch BB, Paz MM (1998) Angew Chem Int Ed 37:1391

    Article  CAS  Google Scholar 

  72. Wagner CE, Shea KJ (2001) Org Lett 3:3063

    Article  CAS  Google Scholar 

  73. Wagner CE, Kim JS, Shea KJ (2003) J Am Chem Soc 125:12179

    Article  CAS  Google Scholar 

  74. Shea KJ, Staiger CL, Lee SY (1999) Macromolecules 32:3157

    Article  CAS  Google Scholar 

  75. Zhou XZ, Shea KJ (2001) Macromolecules 34:3111

    Article  CAS  Google Scholar 

  76. Mondière R, Goddard JP, Carrot G, Gall TL, Mioskowski C (2005) Macromolecules 38:663

    Article  Google Scholar 

  77. Bai J, Shea KJ (2006) Macromolecules 39:7196

    Article  CAS  Google Scholar 

  78. Maruoka K, Oishi M, Yamamoto H (1996) Macromolecules 29:3328

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Material Science and Biotechnology, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, 790-8577, Japan

    Eiji Ihara

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  1. Eiji Ihara
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Correspondence to Eiji Ihara .

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Editors and Affiliations

  1. Dept. Advanced Materials, Hannam University, Jeonmin-Dong 561-6, Taejon, Yuseong-Gu, 305-811, Korea, Republic of (South Korea)

    Kwang-Sup Lee

  2. , R & D Center for Bio-based Materials, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, 606-8585, Japan

    Shiro Kobayashi

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Ihara, E. (2010). Poly(substituted Methylene) Synthesis: Construction of C–C Main Chain from One Carbon Unit. In: Lee, KS., Kobayashi, S. (eds) Polymer Materials. Advances in Polymer Science, vol 231. Springer, Berlin, Heidelberg. https://doi.org/10.1007/12_2009_46

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