The Ba(II) complex of a crown ether bearing a sulphydryl side-arm as turnover catalyst of ester cleavage

Tetrahedron

Volumn 52, Issue 26, 1996, Pages 8867-8876

  Cacciapaglia, Roberta ^a   Mandolini, Luigi ^a   Spadola, Francesco ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CROWN ETHER DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0029895834     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00434-6     Document Type: Article

References (21)

1. a) Chao, Y.; Cram, D.J. J. Am. Chem. Soc. 1976, 98, 1015-1017;
2. b) Chao, Y., Weisman, G.R.; Sogah, G.D.Y.; Cram, D.J. J. Am. Chem. Soc. 1979, 101, 4948-4958.
3. a) Lehn, J.M.; Sirling, C. J. Chem. Soc. Chem. Comm. 1978, 949-951;
4. b) Lehn, J.M.; Sirling, C. New J. Chem. 1987, 11, 693-702.
5. Ercolani, G.; Mandolini, L. J. Am. Chem. Soc. 1990, 112, 423-427.
6. a) Cacciapaglia, R; Lucente, S.; Mandolini, L.; van Doom, A.R.; Reinhoudt, D.N.; Verboom, W. Tetrahedron 1989, 45, 5293-5304;
7. b) Cacciapaglia R.; van Doom, A.R.; Mandolini, L.; Reinhoudt, D.N.; Verboom, W. J. Am. Chem. Soc. 1992, 114, 2611-2617.
8. a) Kraft, D.; Cacciapaglia, R; Böhmer, V.; El-Fadl, A.A.; Harkema, S.; Mandolini, L., Reinhoudt, D.N.; Verboom, W.; Vogt, W. J. Org. Chem. 1992, 57, 826-834;
9. b) Cacciapaglia R.; Mandolini, L.; Reinhoudt, D.N.; Verboom, W. J. Phys. Org. Chem. 1992, 5, 663-669.
10. Cacciapaglia, R.; Casnati, A.; Mandolini, L.; Ungaro, R. J. Am. Chem. Soc. 1992, 114, 10956-10958.
11. Kimura, E.; Nakamura, I.; Koike, T.; Shionoya, M.; Kodama, Y.; Ikeda, T.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 4764-4771.
12. Koike, T.; Kajitani, S.; Nakamura, I.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1995, 117, 1210-1219.
13. The finding that pNPOH is 74% ionised in this medium indicates that the basicity toward neutral acids is the same as that of an aqueous solution having pH 7.6.
14. Fersht, A. Enzyme Structure and Mechanism, W.H. Freeman and Co.: New York, 1985; Chapter 4.
15. Bender, M.L. Mechanisms of Homogeneous Catalysis from Protons to Proteins; Wiley Interscience: New York, 1971; pp.443-446.
16. Cacciapaglia, R., Mandolini, L.; Van Axel Castelli, V.: The Effect of Cation Complexing Agents in the Ba(II) Promoted Basic Ethanolysis of Phenyl Acetate, Proceedings of 2° Congresso Nazionale di Chimica Supramolecolare, Perugia, 7-9 September, 1994.
17. Izatt, R.M.; Pawlak, K.; Bradshaw, J.S.; Bruening, R.L. Chem. Rev. 1991, 91, 1721-2085.
18. Illuminati, G.; Mandolini, L.; Masci, B. J. Am. Chem. Soc. 1981, 103, 4142-4145.
19. Wilcox, C.S.; Babston, R.E. J. Org. Chem. 1984, 49, 1451-1453.
20. S.G. Luxon (ed.), Hazards in the Chemical Laboratory, 5th edn.; The Royal Society of Chemistry: Cambridge, 1992; p. 524.
21. Rastetter, W.H.; Phillion, D.P. J. Org. Chem. 1981, 46, 3204-3208.