Sustainable Polymers from Biomass-Derived α-Methylene-γ-Butyrolactones
Ravikumar R. Gowda
Colorado State University, Fort Collins, Colorado
Search for more papers by this authorEugene Y.-X. Chen
Colorado State University, Fort Collins, Colorado
Search for more papers by this authorRavikumar R. Gowda
Colorado State University, Fort Collins, Colorado
Search for more papers by this authorEugene Y.-X. Chen
Colorado State University, Fort Collins, Colorado
Search for more papers by this authorAbstract
Sustainable polymers based on the biomass-derived renewable α-methylene-γ-butyrolactones, including α-methylene-γ-butyrolactone, γ-methyl-α-methylene-γ-butyrolactone, and β-methyl-α-methylene-γ-butyrolactone, are reviewed. Polymerization methods employed for the synthesis of such polymers are classified into four different categories according to polymerization types or mechanisms: free radical polymerization, coordination polymerization, group-transfer and anionic polymerization, and zwitterionic polymerization. In addition to synthetic methods, polymer properties, polymerization characteristics, as well as polymerization and stereochemical control mechanisms are also described.
Bibliography
- 1 M. Okada, Prog. Polym. Sci. 27, 87–133 (2002).
- 2 C. K. Williams and M. A. Hillmyer, Polym. Rev. 48, 1–10 (2008).
- 3 J. Rass-Hansen, H. Falsig, B. Jorgensen, and C. H. Christensen, J. Chem. Technol. Biotechnol. 82, 329–333 (2007).
- 4G. A. Olah, A. Goeppert, and G. K. S. Prakash, Beyond oil and Gas: The Methanol Economy, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 2006.
- 5 P. B. Weisz, Phys. Today 57, 47–52 (2004).
- 6 J. Zaldivar, J. Nielsen, and L. Olsson, Appl. Microbiol. Biotechnol. 56, 17–34 (2001).
- 7 M. A. R. Meier, J. O. Metzger, and U. S. Schubert, Chem. Soc. Rev. 36, 1788–1802 (2007).
- 8 G. W. Coates and M. A. Hillmyer, Macromolecules 42, 7987–7989 (2009).
- 9 A. Gandini, Macromolecules 41, 9491–9504 (2008).
- 10 A. H. Tullo, Chem. Eng. News 86 (39), 21–25 (2008).
- 11 M. J.-L. Tschan, E. Brulé, P. Haquette, and C. M. Thomas, Polym. Chem. 3, 836–851 (2012).
- 12 M. W. P. C. V. Rossum, M. Alberda, and L. H. W. V. D. Plas, Phytochemistry 49, 723–729 (1998).
- 13 H. M. R. Hoffman and J. Rabe, Angew. Chem., Int. Ed. Engl. 24, 94–110 (1985).
- 14 S. Agarwal, Q. Jin, and S. Maji, ACS Symp. Ser. 1105, 197–212 (2012).
- 15 Y. Kato, H. Yoshida, K. Shoji, Y. Sato, N. Nakajima, and S. Ogita, Tetrahedron Lett. 50, 4751–4753 (2009).
- 16 U.S. Pat. 6,841,627 B2 (2005), C. J. Brandenburg (to E. I. du Pont de Nemours and Company).
- 17 M. K. Akkapeddi, Macromolecules 12, 546–551 (1979).
- 18 U.S. Pat. 2007/0122625 A1 (2007), J. E. Pickett and Q. Ye (to General Electric Company).
- 19 R. R. A. Kitson, A. Millemaggi, and R. J. K. Taylor, Angew. Chem., Int. Ed. Engl. 48, 9426–9451 (2009).
- 20 J.P. Pat. 04049288 A (1992), K. Yokota and T. Hirabayashi (Iwata Kagaku Kogyo K. K., Japan).
- 21 L. E. Manzer, ACS Symp. Ser. 921, 40–51 (2006).
- 22 L. E. Manzer, Appl. Catal. A Gen. 272, 249–256 (2004).
- 23 M. Sauer, D. Porro, D. Mattanovich, and P. Branduardi, Trends Biotechnol. 26, 100–108 (2008).
- 24 C. U. Pittman, Jr. and H. Lee, J. Polym. Sci., Part A: Polym. Chem. 41, 1759–1777 (2003).
- 25 Y. Hu, X. Wang, Y. Chen, L. Caporaso, L. Cavallo, and E. Y.-X. Chen, Organometallics 32, 1459–1465 (2013).
- 26 F. M. A. Geilen, B. Engendahl, A. Harwardt, W. Marquardt, J. Klankermayer, and W. Leitner, Angew. Chem. Int. Ed. 49, 5510–5514 (2010).
- 27 Y. Hu, G. M. Miyake, B. Wang, D. Cui, and E. Y.-X. Chen, Chem. Eur. J. 18, 3345–3354 (2012).
- 28 R. Mullin, Chem. Eng. News 82 (45), 29–37 (2004).
- 29 M. K. Akkapeddi, Polymer 20, 1215–1216 (1979).
- 30 J. W. Stansbury and J. M. Antonucci, Dent. Mater. 8, 270–273 (1992).
- 31 J. Mosnáček, J. A. Yoon, A. Juhari, K. Koynov, and K. Matyjaszewski, Polymer 50, 2087–2094 (2009).
- 32 J. Mosnáček and K. Matyjaszewski, Macromolecules 41, 5509–5511 (2008).
- 33 M. Ueda, M. Takahashi, Y. Imai, and C. U. Pittman, Jr.,, J. Polym. Sci., Polym. Chem. Ed. 20, 2819–2828 (1982).
- 34 WO 00/35960 A2 (2000), A. A. Gridnev and S. D. Ittel (to E. I. du Pont de Nemours and Company).
- 35 D. Y. Sogah, W. R. Hertler, O. W. Webster, and G. M. Cohen, Macromolecules 20, 1473–1488 (1987).
- 36 G. M. Miyake, S. E. Newton, W. R. Mariott, and E. Y.-X. Chen, Dalton Trans. 39, 6710–6718 (2010).
- 37 M. van den Brink, W. Smulders, A. M. van Herk, and A. L. German, J. Polym. Sci., Part A: Polym. Chem. 37, 3804–3816 (1999).
- 38 H. Koinuma, K. Sato, and H. Hirai, Makromol. Chem., Rapid Commun. 3, 311–315 (1982).
- 39 C. Lee and H. K. Hall, Jr., Macromolecules 22, 21–25 (1989).
- 40 D. L. Trumbo, Polym. Bull. 26, 271–275 (1991).
- 41 G. Qi, M. Nolan, F. J. Schork, and C. W. Jones, J. Polym. Sci., Part A: Polym. Chem. 46, 5929–5944 (2008).
- 42 J. Suenaga, D. M. Sutherlin, and J. K. Stille, Macromolecules 17, 2913–2916 (1984).
- 43 R. A. Cockburn, T. F. L. McKenna, and R. A. Macromol. Chem. Phys. 211, 501–509 (2010).
- 44 R. A. Cockburn, R. Siegmann, K. A. Payne, S. Beuermann, T. F. L. McKenna, and R. A. Biomacromolecules 12, 2319–2326 (2011).
- 45 X. Chen, L. Caporaso, L. Cavallo, and E. Y.-X. Chen, J. Am. Chem. Soc. 134, 7278–7281 (2012).
- 46 Y. Hu, X. Xu, Y. Zhang, Y. Chen, and E. Y.-X. Chen, Macromolecules 43, 9328–9336 (2010).
- 47 R. R. Gowda and E. Y.-X. Chen, Dalton Trans. 42, 9263–9273 (2013) .
- 48 G. M. Miyake, Y. Zhang, and E. Y.-X. Chen, Macromolecules 43, 4902–4908 (2010).
- 49 Y. Zhang, L. O. Gustafson, and E. Y.-X. Chen, J. Am. Chem. Soc. 133, 13674–13684 (2011).
- 50 Y. Hu, L. O. Gustafson, H. Zhu, and E. Y.-X. Chen, J. Polym. Sci., Part A. Polym. Chem. 49, 2008–2017 (2011).
- 51 Y. Zhang and E. Y.-X. Chen, Angew. Chem., Int. Ed. Engl. 51, 2465–2469 (2012).
- 52 Y. Zhang, G. M. Miyake, and E. Y.-X. Chen, Angew. Chem., Int. Ed. Engl. 49, 10158–10162 (2010).
- 53 Y. Zhang, G. M. Miyake, M. G. John, L. Falivene, L. Caporaso, L. Cavallo, and E. Y.-X. Chen, Dalton Trans. 41, 9119–9134 (2012).
- 54 WO 03/048220 A2 (2003), C. J. Brandenburg (to E. I. du Pont de Nemours and Company).
- 55 WO 2004/069926 A1 (2004), C. J. Brandenburg (to E. I. du Pont de Nemours and Company).
- 56 WO 2005/028529 A2 (2005), C. J. Brandenburg, L. E. Manzer, and P. Subramanian (to E. I. du Pont de Nemours and Company).
- 57 U.S. Pat. 2008/0293901 A1 (2008), W. H. Ohrbom (to BASF Corporation).
- 58 E.P. Pat. 1,834,968 A1 (2007), K. Sakashita (to Mitsubishi Rayon Co., Ltd).
- 59 E. Y.-X. Chen, Chem. Rev. 109, 5157–5214 (2009).
- 60 U.S. Pat. 2,624,723 (1953), W. J. McGraw and N. J. Morristown (to Allied Chemical & Dye Corporation).
- 61 L. S. Luskin and R. J. Meyers, Encyclopedia of Polymer Science and Technology, Interscience Publishers, New York, 1964, Vol. 1, pp. 264.
- 62 F. A. Bovey, High Resolution NMR of Macromolecules, Academic Press, Inc., New York, 1972, pp. 78.
- 63 L. F. Johnson, F. Heatley, and F. A. Bovey, Macromolecules 3, 175–177 (1970).
- 64 Y. Inoue, A. Nishioka, and R. Chujo, Polym. J. 2, 535–540 (1971).
- 65 I. R. Peat and W. F. Reynolds, Tetrahedron Lett. 14, 1359–1362 (1972).
- 66 F. A. Bovey, J. Polym. Sci. 46, 59–64 (1960).
- 67 T. G. Fox and H. W. Schenko, Polymer 3, 575–584 (1962).
- 68 T. G. Fox, B. S. Garrett, W. E. Goode, S. Gratch, J. F. Kincaid, A. Spell, and J. D. Stroupe, J. Am. Chem. Soc. 80, 1768–1769 (1958).
- 69 M. Fineman and S. D. Ross, J. Polym. Sci. 5, 259–262 (1950).
- 70 S. Agarwal and R. Kumar, Macromol. Chem. Phys. 212, 603–612 (2011).
- 71 R. A. Cockburn, T. F. L. McKenna, and R. A. Hutchinson, Macromol. React. Eng. 5, 404–417 (2011).
- 72 J. Mosnáček and K. Matyjaszewski, Polym. Prepr. 49, 26–27 (2008).
- 73 T. Uno, S. Kawaguchi, M. Kubo, and T. Itoh, J. Power Sources 178, 716–722 (2008).
- 74 Y. Higaki, R. Okazaki, and A. Takahara, ACS Macro Lett. 1, 1124–1127 (2012).
- 75 J. Shin, Y. Lee, W. B. Tolman, and M. A. Hillmyer, Biomacromolecules 13, 3833–3840 (2012).
- 76 A. Juhari, J. Mosnáček, J. A. Yoon, A. Nese, K. Koynov, T. Kowalewski, and K. Matyjaszewski, Polymer 51, 4806–4813 (2010).
- 77 E. Y.-X. Chen, Dalton Trans. 8784–8793 (2009).
- 78 H. Yasuda, Prog. Polym. Sci. 25, 573–626 (2000).
- 79 A. Rodriguez-Delgado and E. Y.-X. Chen, Macromolecules 38, 2587–2594 (2005).
- 80 A. D. Bolig and E. Y.-X. Chen, J. Am. Chem. Soc. 126, 4897–4906 (2004).
- 81 Y. Ning, M. J. Cooney, and E. Y.-X. Chen, J. Organomet. Chem. 690, 6263–6270 (2005).
- 82 G. Stojcevic, H. Kim, N. J. Taylor, T. B. Marder, and S. Collins, Angew. Chem., Int. Ed. 43, 5523–5526 (2004).
- 83 B. Lian, L. Toupet, and J.-F. Carpentier, Chem. Eur. J. 10, 4301–4307 (2004).
- 84 F. Bandermann, M. Ferenz, R. Sustmann, and W. Sicking, Macromol. Symp. 174, 247–253 (2001).
- 85 Y. Li, E. G. Ward, S. S. Reddy, and S. Collins, Macromolecules 30, 1875–1883 (1997).
- 86 J. W. Strauch, J.-L. Fauré, S. Bredeau, C. Wang, G. Kehr, R. Fröhlich, H. Luftmann, and G. Erker, J. Am. Chem. Soc. 126, 2089–2104 (2004).
- 87 J. Jin, W. R. Mariott, and E. Y.-X. Chen, J. Polym. Chem., Part A: Polym. Chem. 41, 3132–3142 (2003).
- 88 H. Frauenrath, H. Keul, and H. Höcker, Macromolecules 34, 14–19 (2001).
- 89 Y. Ning, L. Caporaso, A. Correa, L. O. Gustafson, L. Cavallo, and E. Y.-X. Chen, Macromolecules 41, 6910–6919 (2008).
- 90 B. Lian, C. M. Thomas, C. Navarro, and J.-F. Carpentier, Organometallics 26, 187–195 (2007).
- 91 A. Rodriguez-Delgado, W. R. Mariott, and E. Y.-X. Chen, Macromolecules 37, 3092–3100 (2004).
- 92 H. Nguyen, A. P. Jarvis, M. J. G. Lesley, W. M. Kelly, S. S. Reddy, N. J. Taylor, and S. Collins, Macromolecules 33, 1508–1510 (2000).
- 93 Y. Zhang, Y. Ning, L. Caporaso, L. Cavallo, and E. Y.-X. Chen, J. Am. Chem. Soc. 132, 2695–2709 (2010).
- 94 H. Yasuda, H. Yamamoto, M. Yamashita, K. Yokota, A. Nakamura, S. Miyake, Y. Kai, and N. Kanehisa, Macromolecules 26, 7134–7143 (1993).
- 95 H. Yasuda, H. Yamamoto, K. Yokota, S. Miyake, and A. Nakamura, J. Am. Chem. Soc. 114, 4908–4909 (1992).
- 96 L. S. Boffa and B. M. Novak, Macromolecules 30, 3494–3506 (1997).
- 97 L. S. Boffa and B. M. Novak, Macromolecules 27, 6993–6995 (1994).
- 98 L. Caporaso and L. Cavallo, Macromolecules 41, 3439–3445 (2008).
- 99 S. Tomasi, H. Weiss and T. Ziegler, Organometallics 26, 2157–2166 (2007).
- 100 L. Caporaso, J. Gracia-Budrìa, and L. Cavallo, J. Am. Chem. Soc. 128, 16649–16654 (2006).
- 101 S. Tomasi, H. Weiss, and T. Ziegler, Organometallics 25, 3619–3630 (2006).
- 102 M. Hölscher, H. Keul, and H. Höcker, Macromolecules 35, 8194–8202 (2002).
- 103 R. Sustmann, W. Sicking, F. Bandermann, and M. Ferenz, Macromolecules 32, 4204–4213 (1999).
- 104 P. A. Cameron, V. Gibson, and A. J. Graham, Macromolecules 33, 4329–4335 (2000).
- 105 H. Deng, T. Shiono, and K. Soga, Macromolecules 28, 3067–3073 (1995).
- 106 S. Collins, D. G. Ward, and K. H. Suddaby, Macromolecules 27, 7222–7224 (1994).
- 107 G. M. Miyake, L. Caporaso, L. Cavallo, and E. Y.-X. Chen, Macromolecules 42, 1462–1471 (2009).
- 108 G. M. Miyake and E. Y.-X. Chen, Macromolecules 41, 3405–3416 (2008).
- 109 G. M. Miyake W. R. Mariott, and E. Y.-X. Chen, J. Am. Chem. Soc. 129, 6724–6725 (2007).
- 110 W. R. Mariott, and E. Y.-X. Chen, Macromolecules 38, 6822–6832 (2005).
- 111 W. R. Mariott and E. Y.-X. Chen, Macromolecules 37, 4741–4743 (2004).
- 112 Y. Ning and E. Y.-X. Chen, J. Am. Chem. Soc. 130, 2463–2465 (2008).
- 113 W. J. Evans, J. W. Grate, H. W. Choi, I. Bloom, W. E. Hunter, and J. L. Atwood, J. Am. Chem. Soc. 107, 941–946 (1985).
- 114 S. A. Schuetz, V. W. Day, R. D. Sommer, A. L. Rheingold, and J. A. Belot, Inorg. Chem. 40, 5292–5295 (2001).
- 115 X. Xu, Y. Chen, and J. Sun, Chem. Eur. J. 15, 846–850 (2009).
- 116 X. Xu, Y. Chen, J. Feng, G. Zou, and J. Sun, Organometallics 29, 549–553 (2010).
- 117 B. Wang, D. Cui, and K. Lv, Macromolecules 41, 1983–1988 (2008).
- 118 I. L. Fedushikin, S. Dechert, and H. Schumann, Angew. Chem., Int. Ed. 40, 561–563 (2001).
- 119 W. J. Evans, T. A. Ulibarri, L. R. Chamberlain, J. W. Ziller, and D. Jr. Alvarez, Organometallics 9, 2124–2130 (1990).
- 120 M. Nodono, T. Tokimitsu, S. Tone, T. Makino, and A. Yanangase, Macromol. Chem. Phys. 201, 2282–2288 (2000).
- 121 W. R. Mariott, A. Rodriguez-Delgado, and E. Y.-X. Chen, Macromolecules 39, 1318–1327 (2006).
- 122 R. Gauvin and A. Mortreux, Chem. Commun. 1146–1148 (2005).
- 123 M. Nishiura and Z. Hou, Nature Chem. 2, 257–268 (2010).
- 124 Y. Ning, H. Zhu and E. Y.-X. Chen, J. Organomet. Chem. 692, 4535–4544 (2007).
- 125 X. Yang, C. L. Stern, and T. J. Marks, J. Am. Chem. Soc. 116, 10015–10031 (1994).
- 126
G. J. P. Britovsek,
V. C. Gibson, and
D. F. Wass,
Angew. Chem., Int. Ed. Engl.
38,
428–447
(1999).
10.1002/(SICI)1521-3773(19990215)38:4<428::AID-ANIE428>3.0.CO;2-3 CAS PubMed Web of Science® Google Scholar
- 127 V. C. Gibson and S. K. Spitzmesser, Chem. Rev. 103, 283–315 (2003).
- 128 G. W. Coates, J. Chem. Soc., Dalton Trans. 467–475 (2002).
- 129 G. W. Coates, P. D. Hustad, and S. Reinartz, Angew. Chem., Int. Ed. Engl. 41, 2236–2257 (2002).
- 130 M. Lamberti, M. Mazzeo, D. Pappalardo, and C. Pellecchia, Coord. Chem. Rev. 253, 2082–2097 (2009).
- 131 M. Delferro and T. J. Marks, Chem. Rev. 111, 2450–2485 (2011).
- 132 A. van der Linden, C. J. Schaverien, N. Meijboom, C. Ganter, and A. G. Orpen, J. Am. Chem. Soc. 117, 3008–3021 (1995).
- 133 R. Baumann, W. M. Davis, and R. R. Schrock, J. Am. Chem. Soc. 119, 3830–3831 (1997).
- 134 A. Yeori, I. Goldberg, M. Shuster, and M. Kol, J. Am. Chem. Soc. 128, 13062–13063 (2006).
- 135 S. Gendler, A. L. Zelikoff, J. Kopilov, I. Goldberg, and M. Kol, J. Am. Chem. Soc. 130, 2144–2145 (2008).
- 136 S. Segal, A. Yeori, M. Shuster, Y. Rosenberg, and M. Kol, Macromolecules 41, 1612–1617 (2008).
- 137 A. Cohen, J. Kopilov, I. Goldberg, and M. Kol, Organometallics 28, 1391–1405 (2009).
- 138 K. Press, A. Cohen, I. Goldberg, V. Venditto, M. Mazzeo, and M. Kol, Angew. Chem., Int. Ed. Engl. 50, 3529–3532 (2011).
- 139 J. Zhou, A. M. Schmidt, and H. Ritter, Macromolecules 43, 939–942 (2010).
- 140
G. Odian,
Principles of Polymerization,
4th ed.,
Wiley-Interscience,
Hoboken, NJ, pp.
581,
2004.
10.1002/047147875X Google Scholar
- 141 A. Duda, T. Biela, J. Libiszowski, S. Penczek, P. Dubois, D. Mecerreyes, and R. Jerome, Polym. Degrad. Stab. 59, 215–222 (1998).
- 142 Y. Zhang and E. Y.-X. Chen, Macromolecules 41, 36–42 (2008).
- 143 Y. Zhang and E. Y.-X. Chen, Macromolecules 41, 6353–6360 (2008).
- 144 O. W. Webster, Adv. Polym. Sci. 167, 1–34 (2004).
- 145 O. W. Webster, W. R. Hertler, D. Y. Sogah, W. B. Farnham, T. V. RajanBabu, J. Am. Chem. Soc. 105, 5706–5708 (1983).
- 146
H. L. Hsieh and
R. P. Quirk,
Anionic Polymerization:
Principles and Practical Applications,
Marcel Dekker, Inc.,
New York,
1996.
10.1201/9780585139401 Google Scholar
- 147 D. Baskaran and A. H. E. Müller, Prog. Polym. Sci. 32, 173–219 (2007).
- 148 D. Baskaran, Prog. Polym. Sci. 28, 521–5811 (2003).
- 149 P. Vlček and L. Lochmann, Prog. Polym. Sci. 24, 793–973 (1999).
- 150 C. Zune and R. Jérôme, Prog. Polym. Sci. 24, 631–664 (1999).
- 151 K. Hatada, T. Kitayama, and K. Ute, Prog. Polym. Sci. 13, 189–276 (1988).
- 152 A. Rodriguez-Delgado and E. Y.-X. Chen, J. Am. Chem. Soc. 127, 961–974 (2005).
- 153 T. Dröge and F. Glorius, Angew. Chem. Int. Ed. 50, 6940–6952 (2010).
- 154 P.-C. Chiang and J. W. Bode, RSC Catalysis Series, Royal Society of Chemistry, Cambridge, UK, pp. 399–435, 2010.
- 155 J. L. Moore and T. Rovis, Top. Curr. Chem. 291, 77–144 (2009).
- 156 V. Nair, S. Vellalath, and B. P. Babu, Chem. Soc. Rev. 37, 2691–2698 (2008).
- 157 F. E. Hahn and M. C. Jahnke, Angew. Chem., Int. Ed. 47, 3122–3172 (2008).
- 158 N. Marion, S. Díez-González and S. P. Nolan, Angew. Chem., Int. Ed. 46, 2988–3000 (2007).
- 159 D. Enders, O. Niemeier, and A. Henseler, Chem. Rev. 107, 5606–5655 (2007).
- 160 D. Bourissou, O. Guerret, F. P. Gabbaï, and G. Bertrand, Chem. Rev. 100, 39–91 (2000).
- 161 M. K. Kiesewetter, E. J. Shin, J. L. Hedrick, and R. M. Waymouth, Macromolecules 43, 2093–2107 (2010).
- 162 N. E. Kamber, W. Jeong, R. M. Waymouth, R. C. Pratt, B. G. G. Lohmeijer, and J. L. Hedrick, Chem. Rev. 107, 5813–5840 (2007).
- 163 E. J. Shin, H. A. Brown, S. Gonzalez, W. Jeong, J. L. Hedrick, and R. M. Waymouth, Angew. Chem., Int. Ed. 50, 6388–6391 (2011).
- 164 J. Raynaud, W. N. Ottou, Y. Gnanou, and D. Taton, Chem. Commun. 46, 3203–3205 (2010).
- 165 J. Raynaud, C. Absalon, Y. Gnanou, and D. Taton, J. Am. Chem. Soc. 131, 3201–3209 (2009).
- 166 M. Rodriguez, S. Marrot, T. Kato, S. Stérin, E. Fleury, and A. Baceiredo, J. Organomet. Chem. 692, 705–708 (2007).
- 167 L. Guo and D. Zhang, J. Am. Chem. Soc. 131, 18072–18074 (2009).
- 168 O. Coutelier, M. El Ezzi, M. Destarac, F. Bonnette, T. Kato, A. Baceiredo, G. Sivasankarapillai, Y. Gnanou, and D. Taton, Polym. Chem. 3, 605–608 (2012).
- 169 J. Pinaud, K. Vijayakrishna, D. Taton, and Y. Gnanou, Macromolecules 42, 4932–4936 (2009).
- 170 G. W. Nyce, J. A. Lamboy, E. F. Connor, R. M. Waymouth, and J. L. Hedrick, Org. Lett. 4, 3587–3590 (2002).
- 171 J. Raynaud, A. Ciolino, A. Baceiredo, M. Destarac, F. Bonnette, T. Kato, Y. Gnanou, and D. Taton, Angew. Chem., Int. Ed. 47, 5390–5393 (2008).
- 172 M. D. Scholten, J. L. Hedrick, and R. M. Waymouth, Macromolecules 41, 7399–7404 (2008).
- 173 A. J. Arduengo, III, H. Bock, H. Chen, M. Denk, D. A. Dixon, J. C. Green, W. A. Herrmann, N. L. Jones, M. Wagner, and R. West, J. Am. Chem. Soc. 116, 6641–6649 (1994).
- 174A. J. Arduengo, III, H. V. R. Dias, R. L. Harlow, and M. Kline, J. Am. Chem. Soc. 114, 5530–5534 (1992).
- 175 D. Enders, K. Breuer, U. Kallfass, and T. Balensiefer, Synthesis 1292–1295 (2003).
- 176 D. Enders, K. Breuer, G. Raabe, J. Runsink, J. H. Teles, J.-P. Melder, K. Ebel, and S. Brode, Angew. Chem., Int. Ed. 34, 1021–1023 (1995).
- 177 B. Maji, M. Breugst, and H. Mayr, Angew. Chem., Int. Ed. 50, 6915–6919 (2011).
- 178 A. T. Biju, M. Padmanaban, N. E. Wurz, and F. Glorius, Angew. Chem., Int. Ed. 50, 8412–8415 (2011).
- 179 S.-I. Matsuoka, Y. Ota, A. Washio, A. Katada, K. Ichioka, K. Takagi, and M. Suzuki, Org. Lett. 13, 3722–3725 (2011).
- 180 R. Breslow, J. Am. Chem. Soc. 80, 3719–3726 (1958).
- 181 J. S. J. McCahill, G. C. Welch, and D. W. Stephan, Angew. Chem., Int. Ed. 46, 4968–497 (2007).
- 182 P. A. Chase, G. C. Welch, T. Jurca, and D. W. Stephan, Angew. Chem., Int. Ed. 46, 8050–8053 (2007).
- 183 G. C. Welch and D. W. Stephan, J. Am. Chem. Soc. 129, 1880–1881 (2007).
- 184 P. Spies, G. Erker, G. Kehr, K. Bergander, R. Frohlich, S. Grimme, and D. W. Stephan, Chem. Commun. 5072–5074 (2007).
- 185 G. C. Welch, R. R. S. Juan, J. D. Masuda, and D. W. Stephan, Science 314, 1124–1126 (2006).
- 186 D. W. Stephan and G. Erker, Angew. Chem., Int. Ed. 49, 46–76 (2010).
- 187 D. Chakraborty and E. Y.-X. Chen, Macromolecules 35, 13–15 (2002).
- 188 S. Feng, G. R. Roof and E. Y.-X. Chen, Organometallics 21, 832–839 (2002).
- 189 C. H. Lee, S. J. Lee, J. W. Park, K. H. Kim, B. Y. Lee, and J. S. Oh, J. Mol. Catal., A: Chem. 132, 231–239 (1998).
- 190 G. S. Hair, A. H. Cowley, R. A. Jones, B. G. McBurnett, and A. Voigt, J. Am. Chem. Soc. 121, 4922–4923 (1999).
- 191 E. Y.-X. Chen, Top. Curr. Chem. 334, 239–260 (2013).
- 192 D. S. Johnston, Adv. Polym. Sci. 42, 51–106 (1982).