Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH FRONT

Probing the RAFT Process Using a Model Reaction between Alkoxyamine and Dithioester

Changxi Li A , Junpo He A B , Ying Liu A , Yanwu Zhou A and Yuliang Yang A

A State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University, Shanghai 200433, P. R. China.

B Corresponding author. Email: jphe@fudan.edu.cn

Australian Journal of Chemistry 65(8) 1077-1089 http://dx.doi.org/10.1071/CH12152
Submitted: 11 March 2012  Accepted: 14 April 2012   Published: 24 May 2012

Abstract

A small-molecular model reaction was designed to probe the reversible addition–fragmentation chain transfer (RAFT) process. In this reaction, alkoxyamine releases radicals that react in situ with dithioester through the RAFT process, generating new radicals through the fragmentation of the intermediate radical. The new radicals can be trapped by free 2,2,6,6-tetramethyl-piperidinyl-N-oxyl radicals (TEMPO) from homolysis of alkoxyamine. The overall reaction is the crossover of the leaving groups between alkoxyamine and dithioester. The advantage of this model as a probe of the RAFT process is that it does not involve polymerization-related elementary reactions such as initiation, propagation, and chain length dependent termination. The kinetics of the model reaction were measured using high-performance liquid chromatography, and then fitted by Monte Carlo simulation to estimate rate coefficients. The obtained rate coefficients of addition for various dithioesters fell into a narrow range of 107–108 L mol–1 s–1, whereas the rate coefficient of fragmentation was model-dependent. It was also found that a significant fraction of the dithioester was consumed by an unspecified additional mechanism. A tentative explanation is proposed in which the intermediate radical undergoes a secondary RAFT reaction with dithioesters, forming a secondary intermediate that serves as a radical reservoir.

Graphical Abstract Image


References

[1]  (a) G. Moad, E. Rizzardo, S. H. Thang, Polymer 2008, 49, 1079.
         | CrossRef | 1:CAS:528:DC%2BD1cXitlels7c%3D&md5=03552fa69703a325d5ca3be6a3b68ce2CAS | open url image1
      (b) G. Moad, E. Rizzardo, S. H. Thang, Acc. Chem. Res. 2008, 41, 1133.
         | CrossRef | open url image1
      (c) G. Moad, E. Rizzardo, S. H. Thang, Aust. J. Chem. 2005, 58, 379.
         | CrossRef | open url image1
      (d) G. Moad, E. Rizzardo, S. H. Thang, Aust. J. Chem. 2006, 59, 669.
         | CrossRef | open url image1
      (e) G. Moad, E. Rizzardo, S. H. Thang, Aust. J. Chem. 2009, 62, 1402.
         | CrossRef | open url image1

[2]  S. Perrier, P. Takolpuckdee, J. Polym. Sci. Pol. Chem. 2005, 43, 5347.
         | CrossRef | 1:CAS:528:DC%2BD2MXhtFygtLvI&md5=f57aa438f40f485a1c52e108a421a431CAS | open url image1

[3]  A. Favier, M.-T. Charreyre, Macromol. Rapid Commun. 2006, 27, 653.
         | CrossRef | 1:CAS:528:DC%2BD28XkvFKnt7k%3D&md5=b3c288ef8a882a91b16542cf6cde0438CAS | open url image1

[4]  H. Willcock, R. K. O’Reilly, Polym. Chem. 2010, 1, 149.
         | CrossRef | 1:CAS:528:DC%2BC3cXlt1OhtL0%3D&md5=216b8c507188c7b2666fb8583000250fCAS | open url image1

[5]  M. H. Stenzel, Chem. Commun. 2008, 3486.
         | CrossRef | 1:CAS:528:DC%2BD1cXovV2lurg%3D&md5=1acd4f2e9b3fd07a97a391bb7da3b378CAS | open url image1

[6]  C. Barner-Kowollik, S. Perrier, J. Polym. Sci. Pol. Chem. 2008, 46, 5715.
         | CrossRef | 1:CAS:528:DC%2BD1cXhtVyrsLzK&md5=79c6841eb4762b726d3f60ee65f4cd0aCAS | open url image1

[7]  L. Barner, T. P. Davis, M. H. Stenzel, C. Barner-Kowollik, Macromol. Rapid Commun. 2007, 28, 539.
         | CrossRef | 1:CAS:528:DC%2BD2sXjslWksLw%3D&md5=2d099e13b406e1782ef212755fd36545CAS | open url image1

[8]  (a) C. Barner-Kowollik, M. Buback, B. Charleux, M. L. Coote, M. Drache, T. Fukuda, A. Goto, B. Klumperman, A. B. Lowe, J. B. McLeary, G. Moad, M. J. Monteiro, R. D. Sanderson, M. P. Tonge, P. Vana, J. Polym. Sci. Pol. Chem. 2006, 44, 5809.
         | CrossRef | 1:CAS:528:DC%2BD28XhtVylt7vI&md5=94db7c36ad9bcd2202019cc35a80a6e3CAS | open url image1
      (b) C. Barner-Kowollik, M. L. Coote, T. P. Davis, L. Radom, P. Vana, J. Polym. Sci. Pol. Chem. 2003, 41, 2828.
         | CrossRef | open url image1
      (c) A. R. Wang, S. Zhu, Y. Kwak, A. Goto, T. Fukuda, M. S. Monteiro, J. Polym. Sci. Pol. Chem. 2003, 41, 2833.
         | CrossRef | open url image1

[9]  B. Klumperman, E. T. A. van den Dungen, J. P. A. Heuts, M. J. Monteiro, Macromol. Rapid Commun. 2010, 31, 1846.
         | CrossRef | 1:CAS:528:DC%2BC3cXhtleiu77K&md5=c778d6ebc5f90484779083d17d474e01CAS | open url image1

[10]  J. Chiefari, Y. K. Chong, F. Ercole, J. Krstina, J. Jeffery, T. P. T. Le, R. T. A. Mayadunne, G. F. Meijs, C. L. Moad, G. Moad, E. Rizzardo, S. H. Thang, Macromolecules 1998, 31, 5559.
         | CrossRef | 1:CAS:528:DyaK1cXkvF2gs7k%3D&md5=7b317daf025894dcec376159155980ccCAS | open url image1

[11]  G. Moad, J. Chiefari, Y. K. Chong, J. Krstina, R. T. A. Mayadunne, A. Postma, E. Rizzardo, S. H. Thang, Polym. Int. 2000, 49, 993.
         | CrossRef | 1:CAS:528:DC%2BD3cXmtFemsbs%3D&md5=a1f943c51966d6dc4e7e06baa69f7b09CAS | open url image1

[12]  C. Barner-Kowollik, J. F. Quinn, D. R. Morsley, T. P. Davis, J. Polym. Sci. Pol. Chem. 2001, 39, 1353.
         | CrossRef | 1:CAS:528:DC%2BD3MXislartbo%3D&md5=276828f583c319f1c19801bcbe7f2065CAS | open url image1

[13]  S. Perrier, C. Barner-Kowollik, J. F. Quinn, P. Vana, T. P. Davis, Macromolecules 2002, 35, 8300.
         | CrossRef | 1:CAS:528:DC%2BD38XnvVKltLs%3D&md5=5e3a71ec039b1e6efffd3bea6a37d7abCAS | open url image1

[14]  (a) C. Barner-Kowollik, P. Vana, J. F. Quinn, T. P. Davis, J. Polym. Sci. Pol. Chem. 2002, 40, 1058.
         | CrossRef | 1:CAS:528:DC%2BD38XisFGgsL4%3D&md5=4ce6c2235e67e12a4c18857220177402CAS | open url image1
      (b) L. Barner, J. F. Quinn, C. Barner-Kowollik, P. Vana, T. P. Davis, Eur. Polym. J. 2003, 39, 449.
         | CrossRef | open url image1

[15]  (a) M. L. Coote, L. Radom, J. Am. Chem. Soc. 2003, 125, 1490.
         | CrossRef | 1:CAS:528:DC%2BD3sXjsFKmtQ%3D%3D&md5=7e0dd157649f2c96921ef24f30bed6d9CAS | open url image1
      (b) A. Feldermann, M. L. Coote, M. H. Stenzel, T. P. Davis, C. Barner-Kowollik, J. Am. Chem. Soc. 2004, 126, 15915.
         | CrossRef | open url image1

[16]  (a) M. J. Monteiro, H. de Brouwer, Macromolecules 2001, 34, 349.
         | CrossRef | 1:CAS:528:DC%2BD3MXhtVaisw%3D%3D&md5=674149fcfe3e32035213a2eed03cea7aCAS | open url image1
      (b) M. J. Monteiro, J. Polym. Sci. Pol. Chem. 2005, 43, 3189.
         | CrossRef | open url image1
      (c) H. De Brouwer, M. A. J. Schellekens, B. Klumperman, M. J. Monteiro, A. L. German, J. Polym. Sci. Pol. Chem. 2000, 38, 3596.
         | CrossRef | open url image1
      (d) F. M. Calitz, J. B. McLeary, J. M. McKenzie, M. P. Tonge, B. Klumperman, R. D. Sanderson, Macromolecules 2003, 36, 9687.
         | CrossRef | open url image1
      (e) R. Venkatesh, B. B. P. Staal, B. Klumperman, M. J. Monteriro, Macromolecules 2004, 37, 7906.
         | CrossRef | open url image1

[17]  (a) Y. Kwak, A. Goto, K. Komatsu, Y. Tsujii, Y. Murata, K. Komatsu, T. Fukuda, Macromolecules 2002, 35, 3026.
         | CrossRef | 1:CAS:528:DC%2BD38XhvVGrsbc%3D&md5=40461a9157debdde0ad1c6e4970982f1CAS | open url image1
      (b) Y. Kwak, A. Goto, T. Fukuda, Macromolecules 2004, 37, 1219.
         | CrossRef | open url image1
      (c) Y. Kwak, A. Goto, K. Komatsu, Y. Sugiura, T. Fukuda, Macromolecules 2004, 37, 4434.
         | CrossRef | open url image1

[18]  A. A. Toy, P. Vana, T. P. Davis, C. Barner-Kowollik, Macromolecules 2004, 37, 744.
         | 1:CAS:528:DC%2BD2cXivVSktQ%3D%3D&md5=bbdf425dee6adc11c434fa33c7c2dacaCAS | open url image1

[19]  A. Goto, T. Fukuda, Prog. Polym. Sci. 2004, 29, 329.
         | CrossRef | 1:CAS:528:DC%2BD2cXis1Ghs7w%3D&md5=c3ceb08a3ba9989210db0c04f5e87f7bCAS | open url image1

[20]  A. R. Wang, S. J. Zhu, J. Polym. Sci. Pol. Chem. 2003, 41, 1553.
         | CrossRef | 1:CAS:528:DC%2BD3sXjvVequ7o%3D&md5=7f08e1e8d498e36e7606039455043fa5CAS | open url image1

[21]  P. Vana, T. P. Davis, C. Barner-Kowollik, Macromol. Theor. Simul. 2002, 11, 823.
         | CrossRef | 1:CAS:528:DC%2BD38XptVylsbo%3D&md5=28b304c0d077fc252dc8948be6b11364CAS | open url image1

[22]  M. L. Coote, E. H. Krenske, E. I. Izgorodina, Macromol. Rapid Commun. 2006, 27, 473.
         | CrossRef | 1:CAS:528:DC%2BD28XjvVCntbg%3D&md5=38bb78708b491e5537f4ab6319a50ffdCAS | open url image1

[23]  J. B. Mcleary, M. P. Tonge, B. Klumperman, Macromol. Theor. Simul. 2006, 27, 1233.
         | 1:CAS:528:DC%2BD28XosVelsL0%3D&md5=e132ced06d6b7d53e49296f72377a3b1CAS | open url image1

[24]  C. Barner-Kowollik, J. F. Quinn, T. L. Nguyen, J. P. Heuts, T. P. Davis, Macromolecules 2001, 34, 7849.
         | CrossRef | 1:CAS:528:DC%2BD3MXnsFajtLY%3D&md5=5972574e163da8353122262a19f91ff5CAS | open url image1

[25]  X. Han, J. Fan, J. He, J. Xu, D. Fan, Y. Yang, Macromolecules 2007, 40, 5618.
         | CrossRef | 1:CAS:528:DC%2BD2sXms1equ78%3D&md5=35ba47b0e1b63072ef0df0987a3622e5CAS | open url image1

[26]  (a) Y. K. Chong, J. Krstina, T. P. T. Le, G. Moad, A. Postma, E. Rizzardo, S. H. Thang, Macromolecules 2003, 36, 2256.
         | CrossRef | 1:CAS:528:DC%2BD3sXitVemuro%3D&md5=be1b7c9c3c7f9a31c2251b589d41e6e5CAS | open url image1
      (b) J. Chiefari, J. Krstina, T. P. T. Le, G. Moad, A. Postma, E. Rizzardo, S. H. Thang, Macromolecules 2003, 36, 2273.
         | CrossRef | open url image1

[27]  (a) J. B. McLeary, F. M. Calitz, J. M. McKenzie, M. P. Tonge, R. D. Sanderson, B. Klumperman, Macromolecules 2004, 37, 2383.
         | CrossRef | 1:CAS:528:DC%2BD2cXhslCqurk%3D&md5=4b486d9ed8570e2c89f370f6a7060753CAS | open url image1
      (b) J. B. McLeary, F. M. Calitz, J. M. McKenzie, M. P. Tonge, R. D. Sanderson, B. Klumperman, Macromolecules 2005, 38, 3151.
         | CrossRef | open url image1

[28]  (a) M. L. Coote, C. Barner-Kowollik, Aust. J. Chem. 2006, 59, 712.
         | CrossRef | 1:CAS:528:DC%2BD28XhtFeqsr%2FL&md5=e81dd81ae29f2186ead40cb044550b7aCAS | open url image1
      (b) M. L. Coote, Macromol. Theor. Simul. 2009, 18, 388.
         | CrossRef | open url image1
      (c) M. L. Coote, E. I. Izgorodina, E. H. Krenske, M. Busch, C. Barner-Kowollik, Macromol. Rapid Commun. 2006, 27, 1015.
         | CrossRef | open url image1
      (d) E. I. Izgorodina, M. L. Coote, J. Phys. Chem. A 2006, 110, 2486.
         | CrossRef | open url image1
      (e) M. L. Coote, J. Phys. Chem. A 2005, 109, 1230.
         | CrossRef | open url image1
      (f) M. L. Coote, Macromolecules 2004, 37, 5023.
         | CrossRef | open url image1

[29]  M. L. Coote, L. Radom, Macromolecules 2004, 37, 590.
         | CrossRef | 1:CAS:528:DC%2BD3sXpvVCntb4%3D&md5=676f99f7eb1d79ada5a4d8ef7efe5b5dCAS | open url image1

[30]  M. L. Coote, D. J. Henry, Macromolecules 2005, 38, 1415.
         | CrossRef | 1:CAS:528:DC%2BD2MXms12qug%3D%3D&md5=2d8d83172e48892d79442da9138be9f4CAS | open url image1

[31]  (a) M. L. Coote, D. J. Henry, Macromolecules 2005, 38, 5774.
         | CrossRef | 1:CAS:528:DC%2BD2MXksFeru7k%3D&md5=32b00659ac824b130c0bd3802ef06bd3CAS | open url image1
      (b) L. Nebhani, S. Sinnwell, C. Y. Lin, M. L. Coote, M. H. Stenzel, C. Barner-Kowollik, J. Polym. Sci. Pol. Chem. 2009, 47, 6053.
         | CrossRef | open url image1
      (c) M. L. Coote, E. I. Izgorodina, G. E. Cavigliasso, M. Roth, M. Busch, C. Barner-Kowollik, Macromolecules 2006, 39, 4585.
         | CrossRef | open url image1
      (d) J. L. Hodgson, K. A. Green, M. L. Coote, Org. Lett. 2005, 7, 4581.
         | CrossRef | open url image1

[32]  D. G. Hawthorne, G. Moad, E. Rizzardo, S. H. Thang, Macromolecules 1999, 32, 5457.
         | CrossRef | 1:CAS:528:DyaK1MXksFSnt74%3D&md5=8654a78c6068830d7dc67fa3c416e56bCAS | open url image1

[33]  F. M. Calitz, M. P. Tonge, R. D. Sanderson, Macromolecules 2003, 36, 5.
         | CrossRef | 1:CAS:528:DC%2BD38XpsVSnu74%3D&md5=ebaf3095fc394b3daf4913a454b8bc04CAS | open url image1

[34]  (a) M. Laus, R. Papa, K. Sparnacci, A. Alberti, M. Benaglia, D. Macciantelli, Macromolecules 2001, 34, 7269.
         | CrossRef | 1:CAS:528:DC%2BD3MXms1Ogsr0%3D&md5=3409ebedacb77d50ab379c8d8b8908eaCAS | open url image1
      (b) A. Alberti, M. Benaglia, M. Laus, D. Macciantelli, K. Sparnacci, Macromolecules 2003, 36, 736.
         | CrossRef | open url image1

[35]  (a) M. Buback, T. Junkers, P. Vana, Macromol. Rapid Commun. 2005, 26, 796.
         | CrossRef | 1:CAS:528:DC%2BD2MXkvFCksbY%3D&md5=1fb4550a500ba9677c3f2fdd2211336fCAS | open url image1
      (b) M. Buback, P. Hesse, T. Junkers, P. Vana, Macromol. Rapid Commun. 2006, 27, 182.
         | CrossRef | open url image1
      (c) J. Barth, M. Buback, M. Meiser, P. Vana, Macromolecules 2010, 43, 51.
         | CrossRef | open url image1
      (d) M. Meiser, M. Buback, J. Barth, P. Vana, Polymer 2010, 51, 5977.
         | CrossRef | open url image1

[36]  M. Meiser, J. Barth, M. Buback, P. Vana, Macromolecules 2011, 44, 2474.
         | CrossRef | 1:CAS:528:DC%2BC3MXktFenur8%3D&md5=5cf106cbc0ca9f38779068e098e80d00CAS | open url image1

[37]  W. Meiser, M. Buback, Macromol. Rapid Commun. 2011, 32, 1490.
         | CrossRef | 1:CAS:528:DC%2BC3MXosFCls74%3D&md5=265f7d860bb175c2017f1995e86465eaCAS | open url image1

[38]  A. Alberti, M. Genaglia, H. Fischer, M. Guerra, M. Laus, D. Macciantelli, A. Postman, K. Sparnacci, Helv. Chim. Acta 2006, 89, 2103.
         | CrossRef | 1:CAS:528:DC%2BD28Xht1Whu77N&md5=c4bffddfcc69b776528b264a4d4a53abCAS | open url image1

[39]  E. Chernikova, V. Golubev, A. Filippov, C. Y. Lin, M. L. Coote, Polym. Chem 2010, 1, 1437.
         | CrossRef | 1:CAS:528:DC%2BC3cXhtl2msLnK&md5=5eab60fb602eddc2fbe520a316e37d42CAS | open url image1

[40]  Y. Luo, R. Wang, L. Yang, B. Yu, B. Li, S. Zhu, Macromolecules 2006, 39, 1328.
         | CrossRef | 1:CAS:528:DC%2BD28XmsVWhsQ%3D%3D&md5=fc820ff3f36a6a6bd6f2de5fd81a7895CAS | open url image1

[41]  K. Suzuki, Y. Nishimura, Y. Kanematsu, Y. Masuda, S Satoh, H. Tobita, Macromol. React. Eng. 2012, 6, 17.
         | CrossRef | 1:CAS:528:DC%2BC3MXhtlKgurfF&md5=2602700c6dc5211388c5473052030e28CAS | open url image1

[42]  (a) D. Konkolewicz, B. S. Hawkett, A. Gray-Weale, S. Perrier, Macromolecules 2008, 41, 6400.
         | CrossRef | 1:CAS:528:DC%2BD1cXpvFOhurs%3D&md5=d6bf40e5903442de471027374b416c27CAS | open url image1
      (b) D. Konkolewicz, B. S. Hawkett, A. Gray-Weale, S. Perrier, J. Polym. Sci. Pol. Chem. 2009, 47, 3455.
         | CrossRef | open url image1

[43]  Y. Ao, J. He, X. Han, Y. Liu, X. Wang, D. Fan, J. Xu, Y. Yang, J. Polym. Sci. Pol. Chem. 2007, 45, 374.
         | CrossRef | 1:CAS:528:DC%2BD2sXpsVKlsA%3D%3D&md5=7f983bd3350061086d86b8b8761dd530CAS | open url image1

[44]  (a) H. Fischer, Macromolecules 1997, 30, 5666.
         | CrossRef | 1:CAS:528:DyaK2sXls1CqtLc%3D&md5=9c33a6117657e17b36ecec8dc07b87d2CAS | open url image1
      (b) H. Fischer, Chem. Rev. 2001, 101, 3581.
         | CrossRef | open url image1
      (c) H. Fischer, J. Polym. Sci. Pol. Chem. 1999, 37, 1885.
         | CrossRef | open url image1
      (d) H. Fischer, A. Kramer, S. R. A. Marque, P. Nesvadba, Macromolecules 2005, 38, 9974.
         | CrossRef | open url image1

[45]  (a) K. Ohno, Y. Tsujii, T. Miyamoto, T. Fukuda, M. Goto, K. Kobayashi, T. Akaike, Macromolecules 1998, 31, 1064.
         | CrossRef | 1:CAS:528:DyaK1cXovFyitA%3D%3D&md5=f5d30b8dddbb492e8ad3c876c62a615dCAS | open url image1
      (b) T. Fukuda, M. Goto, K. Ohno, Macromol. Rapid Commun. 2000, 21, 151.
         | CrossRef | open url image1

[46]  (a) Y. Liu, J. He, J. Xu, D. Fan, W. Tang, Y. Yang, Macromolecules 2005, 38, 10332.
         | CrossRef | 1:CAS:528:DC%2BD2MXhtFKrt7fN&md5=3cdbb6e11d1119e1d63968d945ed20f3CAS | open url image1
      (b) J. Xu, J. He, D. Fan, W. Tang, Y. Yang, Macromolecules 2006, 39, 3753.
         | CrossRef | open url image1
      (c) Y. Zhou, J. He, C. Li, L. Hong, Y. Yang, Macromolecules 2011, 44, 8446.
         | CrossRef | open url image1

[47]  C. Li, J. He, Y. Zhou, Y. Gu, Y. Yang, J. Polym. Sci. Pol. Chem. 2011, 49, 1351.
         | CrossRef | 1:CAS:528:DC%2BC3MXhsFemu7k%3D&md5=01ef86cc21ac141f7a70de186c2431c3CAS | open url image1

[48]  Y. Miura, K. Hirota, H. Moto, B. Yamada, Macromolecules 1998, 31, 4659.
         | CrossRef | 1:CAS:528:DyaK1cXktFWisbs%3D&md5=0fbd2079fdfe1ea3222f3448771c719fCAS | open url image1

[49]  A. Favier, B. Luneau, J. Vinas, A. Laissaoui, D. Gigmes, D. Bertin, Macromolecules 2009, 42, 5953.
         | CrossRef | 1:CAS:528:DC%2BD1MXovVemtrY%3D&md5=8329069f026ecb5601900fd7037ea7eeCAS | open url image1

[50]  (a) J. L. Hodgson, L. B. Roskop, M. S. Gordon, C. Y. Lin, M. L. Coote, J. Phys. Chem. A 2010, 114, 10458.
         | CrossRef | 1:CAS:528:DC%2BC3cXhtFSls7jN&md5=9cd0f20e4aec36c71f9ff50ef14dde60CAS | open url image1
      (b) A. Gaudel-Siri, D. Siri, P. Tordo, ChemPhysChem 2006, 7, 430.
         | CrossRef | open url image1
      (c) D. Gigmes, A. Gaudel-Siri, S. R. Marque, D. Bertin, P. Tordo, P. Astolfi, L. Greci, C. Rizzoli, Helv. Chim. Acta 2006, 89, 2312.
         | CrossRef | open url image1

[51]  (a) J. Sobek, R. Martschke, H. Fischer, J. Am. Chem. Soc. 2001, 123, 2849.
         | CrossRef | 1:CAS:528:DC%2BD3MXhsVaks7k%3D&md5=d8c1c522221bcfc5f9b42f0cb46ff464CAS | open url image1
      (b) S. Marque, C. L. Mercier, P. Tordo, H. Fischer, Macromolecules 2000, 33, 4403.
         | CrossRef | open url image1

[52]     (a) Y. Yang, H. Zhang, Monte Carlo Methods in Polymer Science 1993, Ch. 7 (Fudan Press: Shanghai) [in Chinese].
      (b) J. He, H. Zhang, J. Chen, Y. Yang, Macromolecules 1997, 30, 8010.
         | CrossRef | open url image1

[53]  C. Y. Lin, M. L. Coote, Aust. J. Chem. 2009, 62, 1479.
         | CrossRef | 1:CAS:528:DC%2BD1MXhsVers7bL&md5=57ccd8cc1b789407a09fc4961df20170CAS | open url image1

[54]  (a) A. Theis, A. Feldermann, N. Charton, M. H. Stenzel, T. P. Davis, C. Barner-Kowollik, Macromolecules 2005, 38, 2595.
         | CrossRef | 1:CAS:528:DC%2BD2MXhsF2jsLY%3D&md5=7fd4703b7648c28ad8a5357d5e81fa62CAS | open url image1
      (b) T. Junkers, A. Theis, T. P. Davis, M. Buback, M. H. Stenzel, P. Vana, C. Barner-Kowollik, Macromolecules 2005, 38, 9497.
         | CrossRef | open url image1
      (c) A. Theis, A. Feldermann, N. Charton, T. P. Davis, M. H. Stenzel, C. Barner-Kowollik, Polymer 2005, 46, 6797.
         | CrossRef | open url image1

[55]  (a) A. L. J. Beckwith, V. W. Bowry, K. U. Ingold, J. Am. Chem. Soc. 1992, 114, 4983.
         | CrossRef | 1:CAS:528:DyaK38XktVOhu74%3D&md5=248fa2843d4c9ec208778426769cc9d4CAS | open url image1
      (b) V. W. Bowry, K. U. Ingold, J. Am. Chem. Soc. 1992, 114, 4992.
         | CrossRef | open url image1

[56]  L. Li, J. He, Y. Yang, Chem. J. Chinese Univ. 2004, 25, 1174 [in Chinese]. open url image1

[57]  M. Buback, P. Vana, Macromol. Rapid Commun. 2006, 27, 1299.
         | CrossRef | 1:CAS:528:DC%2BD28Xpsl2msbs%3D&md5=880498dea5f73bc7f8e0c399ed2e4c2eCAS | open url image1



Supplementary MaterialSupplementary Material (781 KB) Export Citation