Novel dimeric organotin cations: Highly effective alcohol acetylation catalysts

Organometallics

Volumn 18, Issue 18, 1999, Pages 3555-3557

  Sakamoto, Katsumasa ^a   Hamada, Yuuki ^a   Akashi, Haruo ^a   Orita, Akihiro ^a   Otera, Junzo ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001512070     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990412k     Document Type: Article

References (30)

1. (a) Rochow, E. G.; Seyferth, D. J. Am. Chem. Soc. 1953, 75, 2877 and references therein.
2. (b) Okawara, R.; Rochow, E. G. J. Am. Chem. Soc. 1960, 82, 3285.
3. (c) McGrady, M. M.; Tobias, R. S. Inorg. Chem. 1964, 3, 1157.
4. For recent representative studies on triorganotin cationic species in solution, see: (d) Birchall, T.; Manivannan, V. J. Chem. Soc., Dalton Trans. 1985, 2671.
5. (e) Lambert, J. B.; Kuhlmann, B. J. Chem. Soc., Chem. Commun. 1992, 931.
6. (f) Lambert, J. B.; Ciro, S. M.; Stern, C. L. J. Organomet. Chem. 1995, 499, 49.
7. Wada, M.; Okawara, R. J. Organomet. Chem. 1965, 4, 487.
8. (a) Clark, H. C.; O'Brien, R. J. Inorg. Chem. 1963, 2, 740.
9. (b) Clark, H. C.; O'Brien, R. J.; Pickard, A. L. J. Organomet. Chem. 1965, 4, 43.
10. (a) Wrackmeyer, B.; Kehr, G.; Boese, R. Angew. Chem., Int. Ed. Engl. 1991, 30, 1370.
11. (b) Wrackmeyer, B.; Kehr, G.; Sebald, A.; Kümmerlen, J. Chem. Ber. 1992, 125, 1597.
12. (a) Puff, H.; Reuter, H. J. Organomet. Chem. 1989, 373, 173.
13. (b) Dakternieks, D.; Zhu, H.; Tiekink, E. R. T. J. Organomet. Chem. 1994, 476, 33.
14. Orita, A.; Sakamoto, K.; Hamada, Y.; Mitsutome, A.; Otera, J. Tetrahedron 1999, 55, 2899.
15. (a) Sato, T.; Otera, J.; Nozaki, H. J. Am. Chem. Soc. 1990, 112, 901.
16. (b) Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. Tetrahedron 1991, 47, 9773.
17. 2 followed by dehydration as described in the text): C, 27.09; H, 4.80. Found: C, 26.88; H, 4.67.
18. 2 as the nonhydrated species: C, 27.09; H, 4.80. Found: C, 26.84; H, 4.73.
19. w = 0.059.
20. (a) Puff, H.; Hevendehl, H.; Höfer, K.; Reuter, H.; Shuh, W. J. Organomet. Chem. 1985, 287, 163.
21. (b) Dakternieks, D.; Jurkschat, K.; van Dreumel, S.; Tiekink, E. R. T. Inorg. Chem. 1997, 36, 2023.
22. (a) Yasuda, K.; Okawara, R. J. Organomet. Chem. 1965, 3, 76.
23. (b) Domingos, A. M.; Sheldrick, G. M. J. Chem. Soc., Dalton Trans. 1974, 475.
24. 12a The X-ray analysis of 4 will be reported in a full paper.
25. The Sn-O distance of 2.802 Å has been taken to be Sn-O bonding: Casa, J. S.; Castellano, E. E.; Condori, F.; Couce, M. D.; Sánchez, A.; Sordo, J.; Valera, J. M.; Zuckerman-Schpector, J. J. Chem. Soc., Dalton Trans. 1997, 4421.
26. 119Sn NMR spectrum of 1a gave rise to two very small signals at -162.6 and -134.0 ppm, respectively. These may be attributable to a higher homologue that was formed by further condensation of 1a. The details will be discussed in a full paper.
27. (a) Otera, J. J. Organomet. Chem. 1981, 221, 57.
28. (b) Holecék, J.; Nádvorník, M.; Hnadlír, K.; Lycka, A. J. Organomet. Chem. 1986, 315, 299.
29. 3CN). See: Janz, G. J.; Tomkins, R. P. T. Nonaqueous Electrolytes Handbook; Academic Press: New York, 1972; Vol. 1, p 419.
30. For acylation of alcohols by nonionic organotin Lewis acid catalysts, see ref 6 and the references therein.