Renewable rigid diamines: Efficient, stereospecific synthesis of high purity isohexide diamines

ChemSusChem

Volumn 4, Issue 12, 2011, Pages 1823-1829

  Thiyagarajan, Shanmugam ^a,b   Gootjes, Linda ^a,b   Vogelzang, Willem ^a,b   Van Haveren, Jacco ^a,b   Lutz, Martin ^c   Van Es, Daan S ^a,b  

^a WAGENINGEN UNIVERSITY   (Netherlands)

^b DUTCH POLYMER INSTITUTE DPI   (Netherlands)

^c UTRECHT UNIVERSITY   (Netherlands)

Author keywords

amines; chirality; isomers; polycycles; renewable resources

Indexed keywords

AMIDES; AMINES; CHIRALITY;

BIO-BASED POLYMERS; BIOBASED; CHIRAL BUILDING BLOCKS; HIGH PURITY; HIGH YIELD; IMPROVED SYNTHETIC ROUTE; ISOSORBIDE; POLYCYCLES; RENEWABLE RESOURCE; STEREOSPECIFIC SYNTHESIS;

ISOMERS;

1,4 3,6 DIANHYDROMANNITOL; 1,4-3,6-DIANHYDROMANNITOL; DIAMINE; FUSED HETEROCYCLIC RINGS; ISOSORBIDE; POLYMER;

ARTICLE; CHEMISTRY; ENVIRONMENTAL PROTECTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS; X RAY DIFFRACTION;

BICYCLO COMPOUNDS, HETEROCYCLIC; CONSERVATION OF NATURAL RESOURCES; DIAMINES; ISOSORBIDE; MAGNETIC RESONANCE SPECTROSCOPY; POLYMERS; STEREOISOMERISM; X-RAY DIFFRACTION;

EID: 83455228406     PISSN: 18645631     EISSN: 1864564X     Source Type: Journal    
DOI: 10.1002/cssc.201100398     Document Type: Article

References (43)

1. G. O. Oleksandr, R. S. Dmytro, V. M. Dmitriy, T. A. Andrey, K. V. Komarov, Chem. Rev. 2011, 111, 5506-5568
2. GB1012563, 1965
3. W. C. Tate, G. J. Scruggs, US3223752, 1965
4. F. L. Charbonneau, E. R. Johnson, B. H. Witteler, G. Khanarian, US5959066, 1999
5. F. L. Charbonneau, G. Khanarian, E. R. Johnson, B. H. Witteler, A. J. Flint, US6063495, 2000
6. F. L. Charbonneau, E. R. Johnson, US6063465, 2000
7. V. J. Kurian, Y. Ling, US6737481, 2004
8. J. Thiem, H. Lüders, Starch/Staerke 1984, 36, 170-176
9. J. Thiem, H. Lüders, Polym. Bull. 1984, 11, 365-369.
10. H. R. Kricheldorf, Z. Gomourachvili, Macromol. Chem. Phys. 1997, 198, 3149
11. D. J. Adelman, L. F. Charbonneau, S. Ung, U.S. Patent 6656577
12. M. Okada, Y. Okada, K. Aoi, J. Polym. Sci., Part A Polym. Chem. 1995, 33, 2813
13. M. Okada, K. Tsunoda, K. Tachikawa, K. Aoi, J. Appl. Polym. Sci. 2000, 77, 338.
14. J. Wu, P. Eduard, S. Thiyagarajan, J. van Haveren, D. van Es, C. E. Koning, M. Lutz, F. Célia Guerra, ChemSusChem 2011, 4, 599-603
15. F. Fenouillot, A. Rousseau, G. Colomines, R. Saint-Loup, J. P. Pascault, Prog. Polym. Sci. 2010, 35, 578-622.
16. J. Thiem, Makromol. Chem. 1986, 18 7, 2775- 2785
17. J. Thiem, F. Bachmann, Makromol. Chem. 1991, 192, 2163-2182.
18. L. Jasinska, M. Villani, J. Wu, D. van Es, E. Klop, S. Rastogi, C. E. Koning, Macromolecules 2011, 44, 3458-3466
19. J. Pfeffer, M. Ortelt, E. Spyrou, T. Hass, U. Korek, H. Schmidt, U. Dingerdissen, (Evonik Degussa), WO 2011000585, 2011, [
20. Chem. Abstr. 2011, 154, 89176 ]
21. J. Pfeffer, M. Ortelt, E. Spyrou, T. Hass, U. Korek, H. Schmidt; U. Dingerdissen, (Evonik Degussa), WO 2011000586, 2011; [
22. Chem. Abstr. 2011, 154, 110159 ]
23. E. Spyrou, J. Pfeffer, H. Loesch, M. Ebbing-Ewald, H. Grosse-Beck, (Evonik Degussa), WO 2011000587, 2011 [
24. Chem. Abstr. 2011, 154, 110160 ].
25. R. Montgomery, L. F. Wiggins, J. Chem. Soc. 1946, 393-396
26. V. G. Bashford, L. F. Wiggins, J. Chem. Soc. 1950, 371-374.
27. A. C. Cope, T. Y. Shen, J. Am. Chem. Soc. 1956, 78, 3177-3182.
28. J. Kuszmann, G. Medgyes, Carbohydr. Res. 1980, 85, 259-269
29. T. G. Archibald, K. Baum, Synth. Commun. 1989, 19, 1493-1498.
30. X=number of X atoms in the azide; isohexide diazide formulae amount to 8/6=1.3 (!); see also, H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075
31. Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
32. S. Thiyagarajan, L. Gootjes, W. Vogelzang, J. Wu, J. van Haveren, D. van Es, Tetrahedron 2011, 67, 383-389.
33. S. Imm, S. Bähn, M. Zhang, L. Neubert, H. Neumann, F. Klasovsky, J. Pfeffer, T. Haas, M. Beller, Angew. Chem. 2011, 123, 7741-7745
34. Angew. Chem. Int. Ed. 2011, 50, 7599-7603.
35. T. Catherine, A-W. Sara, Y. Jeffrey, L. Hengyuan, K. Donald S, (Senomyx, INC), WO 2011/002871, 2011.
36. S. Kumar, U. Ramachandran, Tetrahedron 2005, 61, 4141-4148.
37. C. A. G. Haasnoot, F. A. A. M. DeLeeuw, C. Altona, Tetrahedron 1980, 36, 2783-2792.
38. P. Tundo, F. Aricò, G. Gauthier, A. Baldacci, C. R. Chimie 2011, 14, 652-655.
39. Bruker, SAINT-Plus, Bruker AXS Inc., Madison, Wisconsin, USA, 2001.
40. G. M. Sheldrick, SADABS: Area-Detector Absorption Correction, v2.10, 1999, Universität Göttingen, Germany.
41. G. M. Sheldrick, Acta Crystallogr. Sec. A 2008, 64, 112-122.
42. A. L. Spek, Acta Crystallogr. Sec. D 2009, 65, 148-155.
43. These data can be obtained free of charge from http://www.ccdc.cam.ac.uk/ cgi-bin/catreq.cgi.