Synthesis of novel trithiocarbonate and allyl sulfide containing monomers

Polymer Chemistry

Volumn 5, Issue 1, 2014, Pages 62-68

  Fenoli, Christopher R ^a   Bowman, Christopher N ^a,b  

^a UNIVERSITY OF COLORADO   (United States)

^b University of Colorado at Boulder   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONAL GROUPS; SULFUR COMPOUNDS;

ADDITION-FRAGMENTATION; HIGH YIELD SYNTHESIS; LIGHT EXPOSURE; POLYMER NETWORKS; REACTION YIELDS; REVERSIBLE ADDITION; TRITHIO CARBONATES; TRITHIOCARBONATE;

MONOMERS;

EID: 84888876312     PISSN: 17599954     EISSN: 17599962     Source Type: Journal    
DOI: 10.1039/c3py00709j     Document Type: Article

References (27)

1. F. Duus, in Comprehensive Organic Chemistry, ed., D. Barton, and, W. D. Ollis, Pergamon, New York, 1979, vol. 3, p. 342
2. M. Bogemann, S. Peterson, O. E. Schultz and H. Soll, in Methoden der organischen chemie, ed., E. Muller, Houben-Weyl, Berlin, 1955, vol. 9, p. 804
3. H. C. Godt A. E. Wanns J. Org. Chem. 1961 26 4047
4. G. Moad E. Rizzardo S. H. Thang Radical addition-fragmentation chemistry in polymer synthesis Polymer 2008 49 5 1079 1131
5. T. F. Scott A. D. Schneider W. D. Cook C. N. Bowman Photoinduced plasticity in cross-linked polymers Science 2005 308 5728 1615 1617
6. R. Nicolaÿ J. Kamada A. Van Wassen K. Matyjaszewski Responsive Gels Based on a Dynamic Covalent Trithiocarbonate Cross-Linker Macromolecules 2010 43 9 4355 4361
7. C. J. Kloxin T. F. Scott H. Y. Park C. N. Bowman Mechanophotopatterning on a photoresponsive elastomer Adv. Mater. 2011 23 17 1977 1981
8. B. Griese, Radicals in organic synthesis: formation of carbon-carbon bonds, Pergamon Press, Oxford, 1986
9. W. B. Motherwell and D. Crich, Free radical chain reactions in organic synthesis, Academic Press, London, 1992
10. G. F. Meijs E. Rizzardo Makromol. Chem. Rapid Commun. 1988 9 547 551
11. G. F. Meijs E. Rizzardo S. H. Thang Macromolecules 1988 21 3122 3124
12. P. Cacioli D. G. Hawthorne R. L. Laslett E. Rizzardo D. H. Solomon J. Macromol. Sci., Part A: Pure Appl.Chem. 1986 23 839 852
13. 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 H. Thang Living Free-Radical Polymerization by Reversible Addition-Fragmentation Chain Transfer: The RAFT Process Macromolecules 1998 31 16 5559 5562
14. L. Barner T. P. Davis M. H. Stenzel C. Barner-Kowollik Macromol. Rapid Commun. 2007 28 539
15. H. Y. Park C. J. Kloxin A. S. Abuelyaman J. D. Oxman C. N. Bowman Stress Relaxation via Addition-Fragmentation Chain Transfer in High T Macromolecules 2012 45 5640 5646
16. S. Perrier P. Takolpuckdee J. Polym. Sci., Part A: Polym. Chem. 2005 43 5347 5393
17. Comprehensive Organic Chemistry, ed., D. Barton, and, W. D. Ollis, Pergamon PressLtd, Oxford, UK, 1979, vol. 3, pp. 434-436
18. A. Sugawara M. Shirahata S. Sato R. Sato Bull. Chem. Soc. Jpn. 1984 57 3353
19. M. K. Leung D. T. Hsieh K. H. Lee J. C. Liou J. Chem. Res. 1995 478 480
20. D. Chaturvedi A. K. Chaturvedi N. Mishra V. Mishra An efficient, one-pot synthesis of trithiocarbonates from the corresponding thiols using the Mitsunobu reagent Tetrahedron Lett. 2008 49 33 4886 4888
21. A. W. M. Lee W. H. Chan H. C. Wong Synth. Commun. 1988 18 1531
22. N. Aoyagi B. Ochiai H. Mori T. Endo Mild and Efficient One-Step Synthesis of Trithiocarbonates Using Minimum Amount of CS 2 Synlett 2006 4 0636 0638
23. N. Aoyagi T. Endo Functional RAFT agents for radical-controlled polymerization: quantitative synthesis of trithiocarbonates containing functional groups as RAFT agents using equivalent amount of CS2 J. Polym. Sci., Part A: Polym. Chem. 2009 47 14 3702 37093
24. G. F. Meijis E. Rizzardo S. H. Thang Preparation of Controlled Molecular Weight, Olefin-Terminated Polymers by Free Radical Methods. Chain Transfer Using Allylic Sulfides Macromolecules 1988 21 3122 3124
25. D. H. R. Barton D. Crich Tetrahedron Lett. 1984 25 2787
26. W. D. Cook T. L. Schiller F. Chen C. Moorhoff S. H. Thang C. N. Bowman T. F. Scott Effect of Cross-Link Density on Photoplasticity of Epoxide Networks Containing Allylic Dithioether Moieties Macromolecules 2012 45 24 9734 9741
27. G. Moad E. Rizzardo S. H. Thang Radical addition-fragmentation chemistry in polymer synthesis Polymer 2008 49 5 1079 1131