Summary
The oxidative coupling polymerization of racemic 3,3’-dihydroxy-2,2’-dimethoxy-1,1’-binaphthalene with copper(II) chloride-(-)-sparteine [(-)Sp] in methanol at room temperature was carried out and the enantiomer-selectivity during the polymerization was examined. The (R)-monomer preferentially reacted, and the purity of the unreacted monomer reached 80%ee (S) after 15 h, while that of the polymerized monomer gradually decreased from 26%ee (R) as a function of the polymerization. The ratio of the rate constants of both enantiomers, s=k R /k S , was determined to be 2.3. The model coupling reaction of the mono-benzylated (R)-monomer with CuCl2-(-)Sp showed that the R-configuration with respect to the carbon-carbon bonds between the monomer units was selectively constructed during the polymerization.
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Habaue S, Seko T, Okamoto Y (2002) Macromolecules 35:2437
Habaue S, Seko T, Isonaga M, Ajiro T, Okamoto Y (2003) Polym J 35:592
Habaue S, Seko T, Okamoto Y (2003) Polymer 44:7377
Habaue S, Ajiro H, Yoshii Y, Hirasa T (2004) J Polym Sci A Polym Chem 42:4528
The AOCP of 6,6’-dihydroxy-2,2’-binaphthol derivative was also reported: Xie X, Phuan P-W, Kozlowski MC (2003) Angew Chem Int Ed 42:2168
Nakajima M, Miyoshi I, Kanayama K, Hashimoto S, Noji M, Koga K (1999) J Org Chem 64:2264
Nakajima M, Kanayama K, Miyoshi I, Hashimoto S (1995) Tetrahedron Lett 36:9519
Smrčina M, Poláková J, Vyskočil Š, Kočovský P (1993) J Org Chem 58:4534
Smrčina M, Lorenc M, Hanuš V, Sedmera P, Kočovský P (1992) J Org Chem 57:1917
Okamoto Y, Nakano, T (1994) Chem Rev 94:349
Spassky N (1992) Makromol Chem Macromol Symp 53:367
Okamoto Y, Yashima E (1990) Prog Polym Sci 15:263
Tsuruta T (1972) J Polym Sci D 6:179
Pino P (1965) Adv Polym Sci 4:393
Baar CR, Levy CJ, Min EY-J, Henling LM, Day MW, Bercaw JE (2004) J Am Chem Soc 126:8216
Tsuji M, Aoki T, Sakai R, Satoh T, Kaga H, Kakuchi T (2004) J Polym Sci A Polym Chem 42:4563
Spassky N, Wisniewski M, Pluta C, Borgne AL (1996) Macromol Chem Phys 197:2627
Chien JCW, Vizzini JC, Kaminsky W (1992) Makromol Chem Rapid Commun 13:479
Sepulchre M, Spassky N, Mark C, Schurig V (1981) Makromol Chem Rapid Commun 2:261
Okamoto Y, Ohta K, Yuki H (1978) Macromolecules 11:724
Putala M (1999) Enantiomer 4:243
Juárez-Hernandez M, Johnson DV, Holland HL, McNulty J, Capretta A (2003) Tetrahedron Asymmetry 14:289
Kazlauskas RJ (1989) J Am Chem Soc 111:4953
Wu S-H, Zhang L-Q, Chen C-S, Girdaukas G, Sih CJ (1985) Tetrahedron Lett 26:4323
Fujimoto Y, Iwadate H, Ikekawa N (1985) J Chem Soc Chem Commun 1333
Blum J, Gelman D, Aizenshtat Z, Wernik S, Schumann H (1998) Tetrahedron Lett 39:5611
Tsubaki K, Miura M, Morikawa H, Tanaka H, Kawabata T, Furuta T, Tanaka K, Fuji K (2003) J Am Chem Soc 125:16200
Tanaka K, Furuta T, Fuji K, Miwa Y, Taga T (1996) Tetrahedron Asymmetry 7:2199
Zhang Y, Yeung S-M, Wu H, Heller DP, Wu C, Wulff WD (2003) Org Lett 5:1813
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Habaue, S., Ishikawa, K. Oxidative coupling polymerization of racemic 3,3’-dihydroxy-2,2’-dimethoxy-1,1’-binaphthalene with copper(II)-(-)-sparteine complex. Polym. Bull. 55, 243–250 (2005). https://doi.org/10.1007/s00289-005-0434-x
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DOI: https://doi.org/10.1007/s00289-005-0434-x