Comparative reactivities of phosphotriesters toward iodosocarboxylates in cationic micelles

Langmuir

Volumn 12, Issue 9, 1996, Pages 2200-2205

  Moss, Robert A ^a   Kotchevar, Ann T ^a   Park, Byeong D ^a   Scrimin, Paolo ^b  

^a RUTGERS UNIVERSITY   (United States)

^b UNIVERSITY OF TRIESTE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000478330     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la951093e     Document Type: Review

References (29)

1. Moss, R. A.; Alwis, K. W.; Bizzigotti, G. O. J. Am. Chem. Soc. 1983, 105, 681.
2. Moss, R. A.; Alwis, K. W.; Shin, J.-S. J.Am. Chem.Soc. 1984, 106, 2651.
3. Moss, R. A.; Kim, K. Y. J. Am. Chem. Soc. 1988, 108, 788.
4. Moss, R. A.; Chatterjee, S.; Wilk, B. J. Org. Chem. 1986, 51, 4303.
5. Katritzky, A. R.; Duell, B. L.; Durst, H. D.; Knier, B. L. J. Org. Chem. 1988, 53, 3972.
6. Hammond, P. S.; Forster, J. S.; Lieske, C. N.; Durst, H. D. J. Am. Chem. Soc. 1989, 111, 7860.
7. Bunton, C. A.; Robinson, L. J. Org. Chem. 1969, 34, 773.
8. For brief reviews, see: Fendler, J. H.; Fendler, E. J. Catalysis in Micellar and Macromolecular Systems; Academic: New York, 1975; especially pp 150-161. And: Moss, R.A.; Ihara, Y. J. Org. Chem. 1983, 48, 588.
9. For brief reviews, see: Fendler, J. H.; Fendler, E. J. Catalysis in Micellar and Macromolecular Systems; Academic: New York, 1975; especially pp 150-161. And: Moss, R.A.; Ihara, Y. J. Org. Chem. 1983, 48, 588.
10. 6 whereas PNPDPP is ∼474 times more reactive than paraoxon under approximately comparable conditions; see below.
11. "Aggregate reactivity" refers here to the maximum reactivity of a substrate, as observed in aqueous micellar CTACl solution, and includes a component due to the intrinsic reactivity of the phosphotriester, as well as a factor reflecting its ability to bind to or partition into the micellar phase.
12. Moss, R. A.; Zhang, H.; Chatterjee, S.; Krogh-Jespersen, K. Tetrahedron Lett. 1993, 34, 1729.
13. Kotchevar, A. T.; Moss, R. A.; Scrimin, P.; Tecilla, P.; Zhang, H. Tetrahedron Lett, 1994, 35, 4927.
14. Gulick, W. M., Jr.; Geske, D. H. J. Am. Chem. Soc. 1966, 88, 2928.
15. Moss, R. A.; Bhattacharya, S.; Chatterjee, S. J. Am. Chem. Soc. 1989, 111, 3680.
16. Moss, R. A.; Wilk, B.; Krogh-Jespersen, K.; Blair, J. T.; Westbrook, J. D. J. Am. Chem. Soc. 1989, 111, 250.
17. Bunton, C. A.; Nome, F.; Quina, F. H.; Romsted, L. R.Acc. Chem. Res. 1991, 24, 357.
18. -5 M under the conditions of Table 1.
19. References to "entries" in the following discussion refer to Table 4.
20. N2(P) displacement at P or an addition-elimination sequence at P=O.
21. See: Thatcher, G. R.; Kluger, R. Adv. Phys. Org. Chem. 1989, 25, 99. Williams, A. Adv. Phys. Org. Chem. 1992, 27, 1.
22. See: Thatcher, G. R.; Kluger, R. Adv. Phys. Org. Chem. 1989, 25, 99. Williams, A. Adv. Phys. Org. Chem. 1992, 27, 1.
23. For leading references, see: Takasuki, B. K.; Chin, J. J. Am. Chem. Soc. 1995, 117, 8582. Tsubouchi, A.; Bruice, T. C. J. Am. Chem. Soc. 1995, 117, 7399. Moss, R. A.; Park, B. D.; Scrimin, P.; Ghirlanda, G. J. Chem. Soc., Chem. Commun. 1995, 1627. Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1994, 116, 7893.
24. For leading references, see: Takasuki, B. K.; Chin, J. J. Am. Chem. Soc. 1995, 117, 8582. Tsubouchi, A.; Bruice, T. C. J. Am. Chem. Soc. 1995, 117, 7399. Moss, R. A.; Park, B. D.; Scrimin, P.; Ghirlanda, G. J. Chem. Soc., Chem. Commun. 1995, 1627. Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1994, 116, 7893.
25. For leading references, see: Takasuki, B. K.; Chin, J. J. Am. Chem. Soc. 1995, 117, 8582. Tsubouchi, A.; Bruice, T. C. J. Am. Chem. Soc. 1995, 117, 7399. Moss, R. A.; Park, B. D.; Scrimin, P.; Ghirlanda, G. J. Chem. Soc., Chem. Commun. 1995, 1627. Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1994, 116, 7893.
26. For leading references, see: Takasuki, B. K.; Chin, J. J. Am. Chem. Soc. 1995, 117, 8582. Tsubouchi, A.; Bruice, T. C. J. Am. Chem. Soc. 1995, 117, 7399. Moss, R. A.; Park, B. D.; Scrimin, P.; Ghirlanda, G. J. Chem. Soc., Chem. Commun. 1995, 1627. Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1994, 116, 7893.
27. 19,20 either stabilize a pentacoordinate phosphorous oxyanion intermediate or enhance the leaving group ability of the (surfactant) p-nitrophenylate fragment.
28. This derives from comparing 12 with 6, rather than 4; i.e., the comparison is 2-1/1-2.
29. 2O as eluent and detection at 254 run.