Investigations providing a plausible mechanism in the hexamethyldisilazane- catalyzed trimerization of alkyl isocyanates

Tetrahedron

Volumn 67, Issue 7, 2011, Pages 1506-1510

  Roman, Mihaela ^a   Andrioletti, Bruno ^a   Lemaire, Marc ^a   Bernard, Jean Marie ^b   Schwartz, Johannes ^b   Barbeau, Philippe ^b  

^a UNIVERSITÉ LYON 1   (France)

^b Perstorp France ^*  (France)

Author keywords

Alkyl isocyanate; HMDS; Isocyanurate; Low VOC; Mechanism; Organocatalysis; Trimerization

Indexed keywords

ISOCYANIC ACID DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; OLIGOMERIZATION; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; STOICHIOMETRY; SYNTHESIS; TRIMERIZATION;

EID: 78951485989     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.12.013     Document Type: Article

References (30)

1. J.H. Saunders, and K.C. Frisch Polyurethanes, Chemistry and Technology, Part I. Chemistry 1962 Interscience New York, NY S. 69
2. H. Ulrich The Chemistry and Technology of Isocyanates 1996 Wiley New York, NY
3. http://www.bhopal.org/
4. O'Connor, M. J. PCT Int. Appl. U.S. 5,370,908, 1994.
5. Z. Wirpsza Polyurethanes: Chemistry, Technology and Application 1993 Ellis Horwood London
6. J. Horsky, U. Kubanek, J. Marick, and J. Kralicek Chem. Prum. 32 1982 599 603
7. Z. Bukac, and J. Sebenda Chem. Prum. 35 1985 361 363
8. Misawa, H.; Koseki, T. JP 03166255, 1991;
9. Hirabayashi, M.; Ozawa, S. JP 0309907, 1991;
10. Sato, F.; Tateyama, M.; Kurokawa, S. JP 63122748, 1988.
11. Ishikawa, T.; Tanaka, S.; Shidara, M.; Hatsurtori, I.; Takagame, H.; Mashita, K. JP 0187651, 1989;
12. Nagai, H; Komya, T. JP 0187649, 1989;
13. Osturek, R.; Wingler, F.; Geyev, O. DE 3729457, 1989.
14. O. Olkhovyk, and M. Jaroniec J. Am. Chem. Soc. 127 2005 60 61
15. H. Pusztai, G. Vlad, A. Bodor, I.T. Horvath, H.J. Laas, R. Halpaap, and F. Richter Angew. Chem., Int. Ed. 45 2006 107 110
16. Richter, F.; Halpaap, R.; Koecher, J.; Laas, H-J.; WO 2002092656, 2002;
17. H.A. Duong, M.J. Cross, and J. Louie Org. Lett. 6 2004 4679 4681
18. S.R. Foley, G.P.A. Yap, and D.S. Richeson Organometallics 18 1999 4700 4705
19. F. Paul, S. Moulin, O. Piechaczyk, P. Le Floch, and J.A. Osborn J. Am. Chem. Soc. 129 2007 7294 7304
20. J.-S. Tang, and J.G. Verkade Angew. Chem., Int. Ed. Engl. 32 1993 896 898
21. Robin, J. PCT Int. Appl. U.S. 4,412,073, 1983, Rhone-Poulenc;
22. Bernard, J.-M. PCT Int. Appl. WO 2002012366, 2002 and WO 2002053613, 2002.
23. Bernard, J.M. U.S. 7,524,435, 2009.
24. H.J. Niclas, and D. Martin Tetrahedron 34 1977 703 706
25. H. Lu, and J. Cheng J. Am. Chem. Soc. 129 2007 14114 14115
26. M.J. Fuchter, C.J. Smith, M.W.S. Tsang, A. Boyer, S. Saubern, J.H. Ryana, and A.B. Holmes Chem. Commun. 2008 2152 2154
27. A.J. Nielson Inorg. Synth. 27 1990 327 329
28. H.E. Gottlieb, V. Kotlyar, and A. Nudelman J. Org. Chem. 62 1997 7512 7515
29. T. Mizuno, M. Masatoshi, N. Takeo, I. Toshiyuki, and I. Takatohi Synthesis 17 2006 2825 2830
30. M.D. Purgett, W. Deits, and O. Vogl J. Polym. Sci., Pol. Chem. 20 1982 2477 2499