Solvolysis of 1-Arylethyl Tosylates. Kinetic and Stereochemical Tests for Solvent Participation

Journal of the American Chemical Society

Volumn 107, Issue 15, 1985, Pages 4513-4519

  Allen, Annette D ^a   Kanagasabapathy, V M ^a   Tidwell, Thomas T ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845377255     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00301a023     Document Type: Article

References (26)

1. Ingold, C. K. “Structure and Mechanisms in Organic Chemistry”, 1st ed.; Cornell University Press, Ithaca, NY, 1953. (b) Jencks, W. P. Chem. Soc. Rev. 1981, 10, 345–375. (c) Bentley, T. W.; Schleyer, P. v. R. Adv. Phys. Org. Chem. 1977, 14, 1–67. (d) This classification is due to Winstein; see footnote 2 of Schleyer, P. v. R.; Fry, J. L.; Lam, L. K. M.; Lancelot, C. J. J. Am. Chem. Soc. 1970, 92, 2542–2544.
2. Doering, W. v. E.; Zeiss, H. H. J. Am. Chem. Soc. 1953, 75, 4733–4738. (b) For prior discussions of this idea see: Winstein, S.; Grunwald, E.; Jones, H. W. J. Am. Chem. Soc. 1951, 73, 2700–2707, and references therein. See also Streitwieser, A., Jr. “Solvolytic Displacement Reactions”; McGraw-Hill: New York, 1962; pp 66–69.
3. Shafer, S. G.; Harris, J. M. J. Org. Chem. 1981, 46, 2164–2169.
4. Bentley, T. W.; Carter, G. E. J. Am. Chem. Soc. 1982, 104, 5741–5747. (b) Bentley, T. W.; Bowen, C. T.; Morten, D. H.; Schleyer, P. v. R. J. Am. Chem. Soc. 1981, 103, 5466–5475, and references therein. (c) Al-Shali, S. A. I.; Eaborn, C.; Fattah, F. A.; Najim, S. T. J. Chem. Soc., Chem. Commun. 1984, 318–319. (d) Laureillard, J.; Casadevall, A.; Casadevall, E. Helv. Chim. Acta 1984, 67, 352-360; Tetrahedron 1984, 40, 4921–4928.
5. Martin, J. C. Science 1983, 221, 509–514. (b) Forbus, T. R., Jr.; Martin, J. C. J. Am. Chem. Soc. 1979, 101, 5057–5059. (c) See the comments in Chem. Eng. News 1983, 61 (Nov 28), 3; 1984, 62 (May 28), 4, 70; 1985, 63 (Jan 21), 3, 58.
6. Schleyer, P. v. R.; Würthwein, E.-U.; Kaufmann, E.; Clark, T.; Pople, J. A. J. Am. Chem. Soc. 1983, 105, 5930–5932, and references therein. (b) Yamabe, S.; Yamabe, E.; Minato, T. J. Chem. Soc., Perkin Trans. 2 1983, 1881–1884. (c) Raghavachari, K.; Chandrasekhar, J.; Burnier, R. C. J. Am. Chem. Soc. 1984, 106, 3124–3138, and references therein. (d) Carrion, F.; Dewar, M. J. S. J. Am. Chem. Soc. 1984, 106, 3531–3539.
7. Winstein, S.; Robinson, G. C. J. Am. Chem. Soc. 1958, 80, 169–181.
8. Sneen, R. A. Acc. Chem. Res. 1973, 6, 46–53. (b) McLennan, D. J. J. Am. Chem. Soc. 1976, 9, 281–287. (c) Gregoriou, G. A. Tetrahedron Lett. 1976, 4605–4608.
9. Blandamer, M. J.; Robertson, R. E.; Scott, J. M. W.; Vrielink, A. J. Am. Chem. Soc. 1980, 102, 2585–2592. (b) Blandamer, M. J.; Robertson, R. E.; Golding, P. D.; MacNeil, J. M.; Scott, J. M. W. J. Am. Chem. Soc. 1981, 103, 2415–2416.
10. Bentley, T. W.; Carter, G. E. J. Chem. Soc., Faraday Trans. 1, 1982, 78, 1633–1639.
11. Jencks, W. P. Acc. Chem. Res. 1980, 13, 161–169. (b) Richard, J. P.; Rothenberg, M. E.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1361–1372. (c) Richard, J. P.; Jencks, W. P. Acc. Chem. Res. 1984, 106, 1373–1383. (d) Richard, J. P.; Jencks, W. P. Acc. Chem. Res. 1984, 106, 1383–1396. (e) Richard, J. P.; Jencks, W. P. Acc. Chem. Res. 1984, 106, 1396–1401. (f) Sinnott, M. L.; Jencks, W. P. Acc. Chem. Res. 1980, 102, 2026–2032.
12. Katritzky, A. R.; Sakizadeh, K.; Gabrielsen, B.; le Noble, W. J. J. Am. Chem. Soc. 1984, 106, 1879–1880. (b) Katritzky, A. R.; Lopez-Ro-driquez, M. L.; Marquet, J. J. Chem. Soc., Perkin Trans. 2 1984, 349–354. (c) Katritzky, A. R.; Ou, Y. X.; Musumarra, G. J. Am. Chem. Soc. 1983, 1449–1453. (d) Katritzky, A. R.; Musumarra, G. Chem. Soc. Rev. 1984, 13, 47–68.
13. Allen, A. D.; Ambidge, I. C.; Tidwell, T. T. J. Org. Chem. 1983, 48, 4527–4530. (b) Allen, A. D.; Ambidge, I. C.; Che, C.; Micheal, H.; Muir, R. J.; Tidwell, T. T. J. Am. Chem. Soc. 1983, 105, 2343–2350. (c) Jansen, M. P.; Koshy, K. M.; Mangru, N. N.; Tidwell, T. T. J. Org. Chem. 1981, 103, 3863–3867.
14. Goering, H. L.; Briody, R. G.; Sandrock, G. J. Am. Chem. Soc. 1970, 92, 7401–7407. (b) Shiner, V. J., Jr.; Buddenbaum, W. E.; Murr, B. L.; Lamaty, G. J. Am. Chem. Soc. 1968, 90, 418–426. (c) Sneen, R. A.; Robbins, H. M. J. Am. Chem. Soc. 1972, 94, 7868–7876. (d) Shiner, V. J., Jr.; Hartshorn, S. R.; Vogel, P. C. J. Org. Chem. 1973, 38, 3604–3610. (e) Stein, A. R.; Tencer, M.; Moffatt, E. A.; Dawe, R.; Sweet, J. J. Am. Chem. Soc. 1980, 45, 3539–3540. (f) Noyce, D. S.; Virgilio, J. A. J. Am. Chem. Soc. 1972, 37, 2643–2647. (g) Okamoto, K.; Kinoshita, T.; Oshida, T.; Yamamoto, T.; Ito, Y.; Dohi, M. J. Chem. Soc., Perkin Trans. 2 1976, 1617–1626. (h) Okamoto, K.; Takeuchi, K.; Inoue, T. J. Am. Chem. Soc. 1980, 842–848. (i) Hoffmann, H. M. R. J. Chem. Soc. 1965, 6753–6761. (j) Kenyon, J.; Phillips, H.; Taylor, F. M. H. J. Am. Chem. Soc. 1933, 173–178.
15. Bentley, T. W.; Carter, G. E. J. Org. Chem. 1983, 48, 579–584. (b) Paradisi, C.; Bunnett, J. F. J. Am. Chem. Soc. 1981, 103, 946–948. (c) Diaz, A. F.; Lazdins, I.; Winstein, S. J. Org. Chem. 1968, 90, 1904–1905.
16. Stein, A. R.; Dawe, R. D.; Sweet, J. R. Can. J. Chem., submitted for publication.
17. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543–2549. (b) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143–2147.
18. Schadt, F. L.; Bentley, T. W.; Schleyer, P. v. R. J. Am, Chem. Soc. 1976, 98, 7667–7674. (b) Kevill, D. N.; Lin, G. M. L. J. Am, Chem. Soc. 1979, 101, 3916–3919. (c) Kevill, D. N.; Rissmann, T. J. J. Chem. Soc., Perkin Trans. 2 1984, 717–720.
19. Goering, H. L.; Hopf, H. J. Am. Chem. Soc. 1971, 93, 1224–1230. (b) Bone, J. A.; Pritt, J. R.; Whiting, M. C. J. Chem. Soc., Perkin Trans. 2 1975, 1447–1452 (c) McManus, S. P.; Zutaut, S. E. Tetrahedron Lett. 1984, 25, 2859–2862.
20. Creary, X.; Geiger, C. C.; Hilton, K. J. Am. Chem. Soc. 1983, 105, 2851–2858. (b) Creary, X.; Geiger, C. C. J. Am, Chem. Soc. 1982, 104, 4151–4162. (c) Creary, X.; Geiger, C. C. J. Am, Chem. Soc. 1983, 105, 7123–7129. (d) Creary, X. J. Am, Chem. Soc. 1984, 106, 5568–5577. (e) Creary, X., unpublished results privately communicated.
21. Dannenberg, J. J.; Goldberg, B. J.; Barton, J. K.; Dill, K.; Weinwurzel, D. H.; Longas, M. O. J. Am. Chem. Soc. 1981, 103, 7764–7768.
22. Corriu, R. J. P.; Guerin, C.; Moreau, J. J. E. Top. Stereochem. 1984, 15, 43–198.
23. Yamataka, H.; Tamura, S.; Hanafusa, T.; Ando, T. J. Chem. Soc., Chem. Commun. 1984, 362–363.
24. Olah, G. A.; Prakash, G. K. S. Chem. Brit. 1983, 916–926.
25. “Organic Synthesis”, Collect. Vol. 3; Wiley: New York, 1955, pp 200–202. (b) Bachman, G. B.; Lewis, L. L. J. Am. Chem. Soc. 1947, 69, 2022–2023. (c) McBee, E. T.; Sanford, R. A. J. Am. Chem. Soc. 1959, 72, 4053–4055. (d) Taylor, R.; Smith, G. G.; Wetzel, W. H. J. Am. Chem. Soc. 1962, 4817–4824. (e) Taylor, R. J. Chem. Soc. B 1971, 622–627.
26. Allen, A. D.; Rosenbaum, M.; Seto, N. O. L.; Tidwell, T. T. J. Org. Chem. 1982, 47, 4234–4239.