Abstract
Restricted rotation around single bonds in a polymer main chain can generate a stable helix. In order for this to occur, the main chain must consist of bulky repeating units which are all similarly rotated with respect to each other. Polymers which display these features have recently been discovered. They are called atropisomeric polymers. Examples are poly(isocyanides), poly(chloral), and poly(methacrylates) carrying bulky ester substituents. Atropisomeric polymers with an excess of one screw sense can be prepared from optically active monomers. They can also be obtained from achiral monomers by one of the following methods: (i) screw sense selective polymerization using optically active initiators, (ii) screw sense selective copolymerization with small amounts of optically active comonomers, (iii) chromatographic resolution of the racemic polymer of an achiral monomer.
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References
Eliel, E.L., Stereochemistry of Carbon Compounds. McGraw-Hill: New York, 1962; p. 156.
Christie, G.H.; Kenner, J. J. Chem. Soc. 1992, 121, 614
Nolte, R.J.M.; Beijnen, A.J.M. van; Drenth, W. J. Am. Chem. Soc. 1974, 96, 5932.
Beijnen, A.J.M.; Nolte, R.J.M.; Drenth, W.; Hezemans, A.M.F. Tetrahedron 1976, 32, 2017.
Drenth, W.; Nolte, R.J.M. Acc. Chem. Res. 1979, 12, 30.
Corley, L.S.; Vogl, O. Polym.Bull. 1980, 3, 211.
Okamoto, Y.; Suzuki, K.; Ohta, K.; Hatada, K.; Yuki, H. J. Am. Chem. Soc., 1979, 101,4763.
Cram, D.J.; Sogah, D.Y. J. Am. Chem. Soc. 1985, 107, 8301.
Nolte, R.J.M.; Stephany, R.W.; Drenth, W. Recl. Trav. Chim. Pays-Bas 1973,92, 83; Nolte, R.J.M.; Beijnen, A.J.M. van; Zwikker, J.W.; Drenth, W. Polym. Synth. 1985, 9, 81
Millich, F.; Sinclair, R.G. J. Polym. Sci. 1968, C22, 33.
Millich, F. Macrompl, Rev, 1980, 15, 207.
Beijnen, A.J.M. van; Nolte, R.J.M.; Drenth, W. Recl. Trav. Chim. Pays-Bas 1980, 99, 121.
Aslanyan, V.M. J. Polym. Sci. 1968, C16,3145. Brahms, J.; Michelson, A.M.; Van Holde, K.E. J. Mol. Biol, 1966,15,467. Rich, A.; Tinoco, I. J. Am, Chem, SOc. 1960,82,6409.
Tinoco, I. J. Chim, Phys., Phys. Chim. Biol. 1968,65,91.
De Voe, H. J. Chem. Phys. 1964,41,393; De Voe, H. Ibidem 1965, 43, 3199.
Huige, C.J.M., Thesis, Utrecht (1985).
Nolte, R.J.M.; Drenth, W. Recl. Trav. Chim. Pays-Bas 1973, 92, 788.
Nolte, R.J.M.; Zwikker, J.W.; Reedijk, J.; Drenth, W. J. Mol. Catal. 1978,4,423; Beijnen, A.J.M. van; Nolte, R.J.M.; Zwikker, J.W.; Drenth, W. Ibidem 1978, 4, 427.
Beijnen, A.J.M. van; Nolte, R.J.M.; Drenth, W.; Hezemans, A.M.F.; Coolwijk, P.J.F.M. van de Macromolecules 1980,13,1386; Beijnen, A.J.M. van; Nolte, R.J.M.; Naaktgeboren, A.J.; Zwikker, J.W.; Drenth, W.; Hezemans, A.M.F. Ibidem 1983, 16, 1679.
Treichel, P.M. Adv. Organomet. Chem. 1973,11, 21; Yamamoto, Y.; Yamazaki, H. Coord. Chem. Rev.. 1977,8, 225.
Kamer, P.C.J.; Nolte, R.J.M.; Drenth, W., unpublished results.
Basolo, F.; Pearson, R.G. Mechanism of Inorganic Reactions; Wiley: New York, 1967; p. 404.
Nolte, R.J.M; Zomeren, J.A.J. van; Zwikker, J.W. J. Org. Chem. 1978,43,1972.
Visser, H.G.J.; Nolte, R.J.M.; Zwikker, J.W.; Drenth, W. Ibidem 1985,50, 3133 and 3138.
Kagan, H.B., Stereochemistry: Thieme; Stuttgart, 1977; Vol 3, p. 26.
Harada, T.; Cleij, M.C.; Nolte, R.J.M.; Hezemans, A.M.F.; Drenth, W. J. Chem. Soc. Chem. Commun. 1984, 726.
Kamer, P.C.J.; Nolte, R.J.M; Drenth, W. J. Chem. Soc. Chem. Commun. 1986,in press.
Kamer, P.C.J.; Cleij, M.C.; Harada, T.; Nolte, R.J.M.; Drenth, W., manuscript in preparation.
Vogl, O.; Miller, H.C.; Sharkey, W.H. Macromolecules 1972, 5, 658.
Vogl, O.; Corley, L.S. Polym. Preprints 1978,19,210.
Abe, A.; Tasaki, K.; Inomata, K.; Vogl, O. Macromolecules, 1986, 19, 2707.
Vogl, O.; Jay Cox, G.D. Chem. Tech. 1986, 698.
Okamoto, Y.; Suzuki, K.; Yuki, H. J. Polym. Sci. Polym. Chem. Ed. 1980, 18, 3043.
Okamoto, Y.; Shohi, H.; Yuki, H. J. Polym. Sci. Polym. Lett. 1983, 21, 601.
Okamoto, Y.; Ishikura, M.; Hatada, K.; Yukij, H. Polym.J. 1983, 15, 851.
Okamoto, Y.; Shohi, H.; Ishikura, M.; Yuki, H. Abstracts 28th IUPAC Macromolecular Symposium, Amherst, 1982, p. 233.
Frisch, H.L.; Schuerch, C.; Szwarc, M. J. Polvm. Sci. 1953,11,559.
Pino, P. Adv. Polym. Sci. 1965,4,393.
Okamoto, Y.; Okamoto, I.; Yuki, H. J. Polym. Sci. Polym. Lett. 1981, 19, 451.
Visser, H.G.J.; Nolte, R.J.M.; Drenth, W. Macromolecules 1985, 18, 1818.
Cleij, M.C.; Nolte, R.J.M.; Drenth, W., unpublished results.
Visser, H.G.J., Thesis, Utrecht 1983.
Hatada, K.; Shimizu, S.; Yuki, H.; Harris, W.; Vogl, O. Polym. Bull. 1981,4,179.
Yuki, H.; Okamoto, Y.; Okamoto, I. J. Am. Chem. Soc. 1980, 102, 6356.
Okamoto, Y.; Okamoto, I.; Yuki, H. Chem. Lett. 1981, 835.
Okamoto, Y.; Honda, S.; Okamoto, I.; Yuki, H.; Murata, S.; Noyori, R.; Takaya, H. J. Am. Chem. Soc. 1981, 103, 6971.
Okamoto, Y.; Yashima, E.; Hatada, K. J. Chem. SOc. Chem. Commun. 1984, 1051.
Okamoto, Y.; Yashima, E.; Hatada, K.; Mislow, K. J. Org. Chem. 1984,49,557.
Yoshifuji, M.; Toyota, K.; Niitsu, T.; Inamoto, N.; Okamoto, Y.; Aburatani, R. J Chem. Soc. Chem. Commun, 1986, 1550.
Kissener, W.; Vögtle, F. Angew. Chem. 1985, 97, 227.
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Nolte, R.J.M., Drenth, W. (1987). Atropisomeric Polymers. In: Fontanille, M., Guyot, A. (eds) Recent Advances in Mechanistic and Synthetic Aspects of Polymerization. NATO ASI Series, vol 215. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-3989-9_35
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DOI: https://doi.org/10.1007/978-94-009-3989-9_35
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