Pure Appl. Chem., 2009, Vol. 81, No. 4, pp. 667-683
http://dx.doi.org/10.1351/PAC-CON-08-08-26
How to predict changes in solvolysis mechanisms
References
- 1. (a). C. K. Ingold. Structure and Mechanism in Organic Chemistry, 2nd ed., p. 430, Cornell University Press, Ithaca (1969);
- 1. (b). W. P. Jencks. Chem. Soc. Rev. 10, 345 (1981). (http://dx.doi.org/10.1039/cs9811000345)
- 2. Alternative designation ANDN and DN + AN, respectively: R. D. Guthrie, W. P. Jencks. Acc. Chem. Res. 22, 343 (1989). (http://dx.doi.org/10.1021/ar00166a001)
- 3. (a). S. Winstein, E. Clippinger, A. H. Fainberg, R. Heck, G. C. Robinson. J. Am. Chem. Soc. 78, 328 (1956); (http://dx.doi.org/10.1021/ja01583a022)
- 3. (b). S. Winstein, G. C. Robinson. J. Am. Chem. Soc. 80, 169 (1958). (http://dx.doi.org/10.1021/ja01534a045)
- 4. R. Ta-Shma, Z. Rappoport. J. Am. Chem. Soc. 105, 6082 (1983). (http://dx.doi.org/10.1021/ja00357a020)
- 5. D. J. Raber, J. M. Harris, P. v. R. Schleyer. In Ions and Ion Pairs in Organic Reactions, Vol. 2, M. Szwarc (Ed.), pp. 247-374, John Wiley, New York (1974).
- 6. (a). S. Winstein, E. Clippinger, A. H. Fainberg, G. C. Robinson. J. Am. Chem. Soc. 76, 2597 (1954); (http://dx.doi.org/10.1021/ja01638a093)
- 6. (b). S. Winstein, P. E. Klinedinst Jr., G. C. Robinson. J. Am. Chem. Soc. 83, 885 (1961); (http://dx.doi.org/10.1021/ja01465a035)
- 6. (c). S. Winstein, B. Appel, R. Baker, A. Diaz. Chem. Soc. (London), Spec. Publ. Organic Reaction Mechanisms 19, 109 (1965).
- 7. J. P. Richard, T. L. Amyes, M. M. Toteva, Y. Tsuji. Adv. Phys. Org. Chem. 39, 1 (2004). (http://dx.doi.org/10.1016/S0065-3160(04)39001-5)
- 8. (a). H. Mayr, M. Patz. Angew. Chem. 106, 990 (1994); (http://dx.doi.org/10.1002/ange.19941060905)
- 8. (b). H. Mayr, M. Patz. Angew. Chem., Int. Ed. Engl. 33, 938 (1994). (http://dx.doi.org/10.1002/anie.199409381)
- 9. (a). H. Mayr, T. Bug, M. F. Gotta, N. Hering, B. Irrgang, B. Janker, B. Kempf, R. Loos, A. R. Ofial, G. Remennikov, H. Schimmel. J. Am. Chem. Soc. 123, 9500 (2001); (http://dx.doi.org/10.1021/ja010890y)
- 9. (b). H. Mayr, B. Kempf, A. R. Ofial. Acc. Chem. Res. 36, 66 (2003); (http://dx.doi.org/10.1021/ar020094c)
- 9. (c). H. Mayr, A. R. Ofial. In Carbocation Chemistry, G. A. Olah, G. K. S. Prakash (Eds.), Chap. 13, pp. 331-358, John Wiley, Hoboken (2004);
- 9. (d). A. R. Ofial, H. Mayr. Macromol. Symp. 215, 353 (2004); (http://dx.doi.org/10.1002/masy.200451127)
- 9. (e). H. Mayr, A. R. Ofial. Pure Appl. Chem. 77, 1807 (2005); (http://dx.doi.org/10.1351/pac200577111807)
- 9. (f). H. Mayr, A. R. Ofial. J. Phys. Org. Chem. 21, 584 (2008). (http://dx.doi.org/10.1002/poc.1325)
- 10. S. Minegishi, S. Kobayashi, H. Mayr. J. Am. Chem. Soc. 126, 5174 (2004). (http://dx.doi.org/10.1021/ja031828z)
- 11. P. K. Das. Chem. Rev. 93, 119 (1993). (http://dx.doi.org/10.1021/cr00017a007)
- 12. T. V. Pham, R. A. McClelland. Can. J. Chem. 79, 1887 (2001). (http://dx.doi.org/10.1139/cjc-79-12-1887)
- 13. (a). R. A. McClelland, V. M. Kanagasabapathy, S. Steenken. J. Am. Chem. Soc. 110, 6913 (1988); (http://dx.doi.org/10.1021/ja00228a066)
- 13. (b). R. A. McClelland. Reactive Intermediates, R. A. Moss, M. S. Platz, M. Jones Jr. (Eds.), Chap. 1, pp. 3-40, John Wiley, Hoboken (2004).
- 14. (a). B. Denegri, S. Minegishi, O. Kronja, H. Mayr. Angew. Chem. 116, 2353 (2004); (http://dx.doi.org/10.1002/ange.200353468)
- 14. (b). B. Denegri, S. Minegishi, O. Kronja, H. Mayr. Angew. Chem., Int. Ed. 43, 2302 (2004); (http://dx.doi.org/10.1002/anie.200353468)
- 14. (c). T. B. Phan, H. Mayr. Can. J. Chem. 83, 1554 (2005). (http://dx.doi.org/10.1139/v05-170)
- 15. D. N. Kevill. In Advances in Quantitative Structure-Property Relationships, Vol. 1, M. Charton (Ed.), pp. 81-115, JAI Press, Greenwich (1996).
- 16. H. F. Schaller, A. A. Tishkov, X. Feng, H. Mayr. J. Am. Chem. Soc. 130, 3012 (2008). (http://dx.doi.org/10.1021/ja0765464)
- 17. S. Minegishi, R. Loos, S. Kobayashi, H. Mayr. J. Am. Chem. Soc. 127, 2641 (2005). (http://dx.doi.org/10.1021/ja045562n)
- 18. T. W. Bentley. Prog. Phys. Org. Chem. 17, 121 (1990). (http://dx.doi.org/10.1002/9780470171967.ch5)
- 19. (a) ref. [5]; (b) P. J. Stang, Z. Rappoport, M. Hanack, L. R. Subramanian. Vinyl Cations, Chap. 6, pp. 337-338, Academic Press, New York (1979); (c) Z. Rappoport. In Reactive Intermediates, Vol. 3, R. A. Abramovitch (Ed.), pp. 583-594, Plenum Press: New York (1983); (d) T. Kitamura, H. Taniguchi, Y. Tsuno. In Dicoordinated Carbocations, Z. Rappoport, P. J. Stang (Eds.), pp. 321-376, John Wiley, Chichester (1997).
- 20. (a). T. H. Bailey, J. R. Fox, E. Jackson, G. Kohnstam, A. Queen. J. Chem. Soc., Chem. Commun. 122 (1966);
- 20. (b). L. C. Bateman, M. G. Church, E. D. Hughes, C. K. Ingold, N. A. Taher. J. Chem. Soc. 979 (1940); (http://dx.doi.org/10.1039/jr9400000979)
- 20. (c). C. K. Ingold. Structure and Mechanism in Organic Chemistry, 2nd ed., p. 492, Cornell University Press, Ithaca (1969).
- 21. (a). B. Denegri, A. Streiter, S. Juric, A. R. Ofial, O. Kronja, H. Mayr. Chem.Eur. J. 12, 1648 (2006); (http://dx.doi.org/10.1002/chem.200500845)
- 21. (b). B. Denegri, A. Streiter, S. Juric, A. R. Ofial, O. Kronja, H. Mayr. Chem.Eur. J. 12, 5415 (2006). (http://dx.doi.org/10.1002/chem.200690066)
- 22. B. Denegri, A. R. Ofial, S. Juric, A. Streiter, O. Kronja, H. Mayr. Chem.Eur. J. 12, 1657 (2006). (http://dx.doi.org/10.1002/chem.200500847)
- 23. T. W. Bentley. Chem.Eur. J. 12, 6514 (2006). (http://dx.doi.org/10.1002/chem.200600517)
- 24. (a). B. Denegri, O. Kronja. J. Org. Chem. 72, 8427 (2007); (http://dx.doi.org/10.1021/jo701379n)
- 24. (b). S. Juric, O. Kronja. J. Phys. Org. Chem. 21, 108 (2008). (http://dx.doi.org/10.1002/poc.1290)
- 25. (a). H. Mayr, S. Minegishi. Angew. Chem. 114, 4674 (2002); (http://dx.doi.org/10.1002/1521-3757(20021202)114:23<4674::AID-ANGE4674>3.0.CO;2-Y)
- 25. (b). H. Mayr, S. Minegishi. Angew. Chem., Int. Ed. 41, 4493 (2002). (http://dx.doi.org/10.1002/1521-3773(20021202)41:23<4493::AID-ANIE4493>3.0.CO;2-U)
- 26. (a). H. F. Schaller, H. Mayr. Angew. Chem. 120, 4022 (2008); (http://dx.doi.org/10.1002/ange.200800354)
- 26. (b). H. F. Schaller, H. Mayr. Angew. Chem., Int. Ed. 47, 3958 (2008). (http://dx.doi.org/10.1002/anie.200800354)
- 27. G. S. Hammond. J. Am. Chem. Soc. 77, 334 (1955). (http://dx.doi.org/10.1021/ja01607a027)
- 28. (a). R. A. Marcus. J. Phys. Chem. 72, 891 (1968); (http://dx.doi.org/10.1021/j100849a019)
- 28. (b). W. J. Albery. Annu. Rev. Phys. Chem. 31, 227 (1980). (http://dx.doi.org/10.1146/annurev.pc.31.100180.001303)
- 29. (a). E. Grunwald, S. Winstein. J. Am. Chem. Soc. 70, 846 (1948); (http://dx.doi.org/10.1021/ja01182a117)
- 29. (b). A. H. Fainberg, S. Winstein. J. Am. Chem. Soc. 78, 2770 (1956). (http://dx.doi.org/10.1021/ja01593a033)
- 30. T. W. Bentley, K. Roberts. J. Org. Chem. 50, 4821 (1985). (http://dx.doi.org/10.1021/jo00224a034)
- 31. E. M. Arnett, C. Petro, P. v. R. Schleyer. J. Am. Chem. Soc. 101, 522 (1979).
- 32. (a). J. P. Richard, W. P. Jencks. J. Am. Chem. Soc. 104, 4689 (1982); (http://dx.doi.org/10.1021/ja00381a037)
- 32. (b). J. P. Richard, W. P. Jencks. J. Am. Chem. Soc. 104, 4691 (1982). (http://dx.doi.org/10.1021/ja00381a038)