Mechanism of tin(IV) -catalysed urethane formation

Journal of Organometallic Chemistry

Volumn 518, Issue 1-2, 1996, Pages 21-27

  Houghton, Roy P ^a   Mulvaney, Andrew W ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

Tin carboxylates; Tin thiolates; Urethane formation

Indexed keywords

EID: 0030581048     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0022-328X(96)06223-7     Document Type: Article

References (50)

1. [1] A. Farkas and G.A. Mills, Adv. Catal, 13 (1962) 393.
2. [2] F. Hostettler and E.F Cox, Ind. Eng. Chem., 52 (1960) 609.
3. [3] K. Schwetlick, R. Noack and F. Stebner, J. Chem. Soc., Perkin Trans. 2 (1994) 599.
4. [4] S.G. Entelis, O.V. Nesterov and V.B. Zabrodin, Kinet. i Katal., 7 (1966) 627; Chem. Abstr., 65 (1966) 18478.
5. [4] S.G. Entelis, O.V. Nesterov and V.B. Zabrodin, Kinet. i Katal., 7 (1966) 627; Chem. Abstr., 65 (1966) 18478.
6. [5] (a) J. Holecek, M. Nadvornik and K. Handlir, J. Organomet. Chem., 315 (1986) 299.
7. (b) N. Samsodin, S.W. Ng and V.G. Kumar Das, Chemistry and Technology of Silicon and Tin, Oxford University Press, 1992, p. 599.
8. (c) A.S. Mufti and R.C. Poller, J. Chem. Soc., C, (1967) 1362.
9. (d) S.W. Ng, Z.A. Chen Wei, V.G. Kumar Das, W.H. Yip, R.-J. Wang and T.C.W. Mak, J. Cryst. Spectrosc. Res., 21 (1991) 39.
10. [6] (a) R.S. Bruenner and A.E. Oberth, J. Org. Chem., 31 (1966) 887.
11. (b) A.E. Oberth and R.S. Bruenner, Ind. Eng. Chem. Fundam., 8 (1969) 383.
12. [7] A.J. Bloodworth and A.G. Davies, J. Chem. Soc., C, (1966) 5238.
13. [8] (a) F.W. Van Der Weij, J. Polym. Sci., Polym. Chem., 19 (1981) 381.
14. (b) J. Robins, B.H. Edwards and S.K. Tokach, Adv. Urethane Sci. Technol., 9 (1984) 65.
15. (c) E.P. Squiller and J.W. Rosthauser, Modern Paints and Coatings, June (1987) 28.
16. [9] (a) J.-J. Tondeur, G. Vandendunghen and M. Watelet, J. Chem. Res. (M), (1992) 3039;
17. (b) 2024.
18. [10] (a) R. Bacaloglu, L. Cotarca, N. Marcu and St. Tölgyi, J. Prac. Chem., 330 (1988) 54 1.
19. (b) J. Robins, J. Appl. Polym. Sci., 9 (1965) 821.
20. (c) J.W. Britain and P.G. Gemeinhardt, J. App. Polym. Sci., 4 (1960) 207.
21. [11] K. Wongkamolsesh and J.E. Kresta, Urethane Chemistry and Applications, ACS Symp. Ser. Vol. 270, 1985, p. 111.
22. [12] S.G. Entelis and O.V. Nesterov, Kinet. i Katal., 7 (1966) 464; Chem. Abstr., 65 (1966) 10462.
23. [12] S.G. Entelis and O.V. Nesterov, Kinet. i Katal., 7 (1966) 464; Chem. Abstr., 65 (1966) 10462.
24. [13] A.W. Mulvaney, Ph.D. Thesis, University of Wales, 1995.
25. [14] J.D. Kennedy and W.J. McFarlane, Chem. Soc., Perkin Trans. 2, (1974) 146.
26. [15] A similar retarding effect of carboxylic acids has been noted in the catalysis of the polymerization of lactide by tin(II) diesters. This reaction also is thought to involve the formation of a catalytically active tin alkoxide as the result of alcoholysis of the starting tin diester; X. Zhang, D.A. Macdonald, M.F.A. Goosen and K.B. McAuley, J. Polym. Sci., Polym. Chem., 32 (1994) 2965.
27. [16] Kirk Othner Encyclopedia of Chemical Technology, Vol. 23, Wiley, New York, 3rd edn., 1983, p. 589.
28. [17] R.K. Ingham, S.D. Rosenberg and H. Gilman, Chem. Rev., 60 (1960) 459.
29. [18] D. Sukhani, V.D. Gupta and R.C. Mehrotra, J. Organomet. Chem., 7 (1967) 85.
30. [19] (a) W.D. Honnick and J.J. Zuckerman, J. Organomet. Chem., 178 (1979) 133.
31. (b) T.N. Mitchell, J. Organomet. Chem., 59 (1973) 189.
32. [20] (a) Y. Iwakura and H. Okada, Can. J. Chem., 38 (1960) 2418.
33. (b) J.F. Smith and E.C. Friedrich, J. Org. Chem., 81 (1959) 161.
34. (c) E. Dyer and J.F. Glenn, J. Am. Chem. Soc., 79 (1959) 366.
35. [21] A. Pushpa Rupani, A. Singh and R.C. Mehrotra, J. Organomet. Chem., 185 (1980) 209.
36. [22] (a) C. Naegeli and Y. Tyabji, Helv. Chim. Acta., 17 (1934) 931;
37. (b) 18 (1935) 142.
38. [23] (a) M.A. Delmas, J.C. Maire, W. McFarlane and Y. Richard, J. Organomet. Chem., 87 (1975) 285.
39. (b) J.D. Kennedy, W. McFarlane and G.S. Pyne, Bull. Soc. Chim. Belg., 84 (1975) 289.
40. (c) A.G. Davies, S.D. Slater, D.C. Povey and G.W. Smith, J. Organomet. Chem., 352 (1988) 283.
41. [24] P.A. Bates, M.B. Hursthouse, A.G. Davies and S.D. Slater, J. Organomet. Chem., 325 (1987) 129.
42. [25] T.B. Grindley and R. Thangarasa, J. Am. Chem. Soc., 112 (1990) 1364.
43. [26] J.R. Horder and M.F. Lappert, J. Chem. Soc., A, (1968) 2004.
44. [27] C. Owens, J.M. Woods. K. Filo, L.L. Pytlewski, D.E. Chasan and N.M. Karayannis, Inorg. Chim. Acta, 37 (1979) 89.
45. [28] D.S. Bystrov, T.N. Sumarokava and V.N. Filiminov, Optic. Spectrosc., 9 (1960) 239.
46. [29] S.G. Entelis, O.V. Nesterov and R.P. Tiger, DAN UUSSR, 178 (1968) 661.
47. [30] P.J. Smith and A.P. Tupiauskas, Ann. Rep. NMR Spectrosc., 8 (1978) 291.
48. [31] (a) S. Roelens and M. Taddei, J. Chem. Soc., Perkin Trans. 2, (1985) 799.
49. (b) P.J. Smith, R.F.M. White and L. Smith, J. Organomet. Chem., 40 (1972) 341.
50. (c) A.C. Chapman, A.G. Davies, P.G. Harrison and W. McFarlane, J. Chem. Soc., C, (1970) 821.