Effect of Cation-Complexing Agents on the Ba(II)-Assisted Basic Ethanolysis of Phenyl Acetate: From Cation Deactivation to Cation Activation

Journal of Organic Chemistry

Volumn 62, Issue 10, 1997, Pages 3089-3092

  Cacciapaglia, Roberta ^a   Mandolini, Luigi ^a   Van Castelli, Valeria Axel ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001363715     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9619995     Document Type: Article

References (16)

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8. Cacciapaglia, R.; Mandolini, L. Chem. Soc. Rev. 1993, 22, 221.
9. Cacciapaglia, R.; Mandolini, L.; Reinhoudt, D. N.; Verboom, W. J. Phys. Org. Chem. 1992, 5, 663.
10. 4NOEt showed a reduced tendency to yield a crystalline material on standing (see ref 10).
11. Kraft, D.; Cacciapaglia, R.; Böhmer, V.; Abu El-Fadl, A.; Harkema, S.; Mandolini, L.; Reinhoudt, D. N.; Verboom, W.; Vogt, W. J. Org. Chem. 1992, 57, 826.
12. No binding data to barium ion in EtOH are available for these ligands in the extensive compilation published by Izatt and co-workers (ref 12), where the following log K values in MeOH at 25 °C are reported: 2.2.2, 12.9; 18C6, 7.3; 15C5, 4.1 (1) and 2.6 (2); 12C4, 2.6 (1) and 2.4 (2). (1) and (2) refer to 1:1 and 2:1 ligand-metal complexes, respectively. It is assumed that the known data in MeOH can be taken as useful approximations for the unknown data in EtOH.
13. Izatt, R. M.; Pawlak, K.; Bradshaw, J. S.; Breuning, R. L. Chem. Rev. 1991, 91, 1721.
14. Interestingly, the 222 cryptate of potassium ion has been reported to act as a catalyst in the reaction of ethoxide ion with p-nitrophenyl methanesulfonate in ethanol: Pregel, M. J.; Buncel, E. J. Am. Chem. Soc. 1993, 115, 10.
15. We have deliberately avoided the use of the expression "ligand-accelerated catalysis" (LAC), because the concept of LAC, as defined and thoroughly discussed by Sharpless and co-workers (ref 15) in the context of asymmetric reactions catalyzed by transition metals, is not strictly applicable to our system.
16. Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1995, 34, 1059.