Synthesis of esters from silyl ethers and acyl chlorides: Catalysis by quaternary ammonium chlorides

Acta Chemica Scandinavica

Volumn 51, Issue 9, 1997, Pages 953-957

  Brandänge, Svante ^a   Leijonmarck, Hans ^a   Minassie, Teclay ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 3242864678     PISSN: 0904213X     EISSN: None     Source Type: Journal    
DOI: 10.3891/acta.chem.scand.51-0953     Document Type: Article

References (24)

1. Rühlmann, K. Z. Chem. 5 (1965) 130 and references therein.
2. Kim, S. and Lee, W. J. Synth. Commun. 16 (1986) 659.
3. Oriyama, T., Oda, M., Gono, J. and Koga, G. Tetrahedron Lett. 35 (1994) 2027.
4. Ganem, B. and Small, V. R. J. Org. Chem. 39 (1974) 3728.
5. Voaden, D. J. and Waters, R. M. Org. Prep. Proced. Int. 8 (1976) 227.
6. Miyashita, M., Shiina, I., Miyoshi, S. and Mukaiyama, T. Bull. Chem. Soc. Jpn. 66 (1993) 1516.
7. Fuchs, E.-F. and Lehmann, J. Chem. Ber. 107 (1974) 721.
8. Aubert, C. and Bégué, J.-P. Synthesis (1985) 759 .
9. Harpp, D. N., Friedlander, B. T., Larsen, C., Steliou, K. and Stockton, A. J. Org. Chem. 43 (1978) 3481.
10. Corey, E. J. and Venkateswarlu, A. J. Am. Chem. Soc. 94 (1972) 6190.
11. Danishefsky, S. J. and Hungate, R. J. Am. Chem. Soc. 108 (1986) 2486.
12. Harpp, D. N. and Gingras, M. J. Am. Chem. Soc. 110 (1988) 7737.
13. Nagashima. N. and Ohno, M. Chem. Pharm. Bull. 39 (1991) 1972.
14. Swain, C. G. and Scott, C. B. J. Am. Chem. Soc. 75 (1953) 246. Swain and Scott found that benzoyl chloride is hydrolysed 88 times faster than benzoyl fluoride in water-acetone.
15. Miller, J. and Ying, O.-L. J. Chem. Soc., Perkin Trans. 2 (1985) 323. Miller and Ying found a rate ratio of 167 for the reaction of 2-propanol with PhCOCl or PhCOF.
16. Armitage, D. A. In: Wilkinson, G., Ed., Comprehensive Organometallic Chemistry, Vol. 2, 1982, p. 13.
17. Byun, H.-S., Kumar, E. R. and Bittman, R. J. Org. Chem. 59 (1994) 2630.
18. Martin, S. F., Josey, J. A., Wong, Y.-L. and Dean, D. W. J. Org. Chem. 59 (1994) 4805.
19. Burgos, C. E., Ayer, D. E. and Johnson, R. A. J. Org. Chem. 52 (1987) 4973.
20. Vasilenko, I. A., Serebrennikova, G. A. and Evstigneeva, R. P. Bioorg. Chem. USSR 1 (1975) 39.
21. Aoki, T. and Poulter, C. D. J. Org. Chem. 50 (1985) 5634.
22. Hirth, G. and Barner, R. Helv. Chim. Acta 65 (1982) 1059.
23. Bronson, J. J., Ghazzouli, I., Hitchcock, M. J. M., Webb, R. R. Jr. and Martin, J. C. J. Med Chem. 32 (1989) 1457.
24. Johansson, G., Percec, V., Ungar, G. and Abramic, D. J. Chem. Soc., Perkin Trans. 1 (1994) 447.