Effects of adjacent onium cations and remote substituents on the H-A+ bond equilibrium acidities in dimethyl sulfoxide solution. An extensive ylide thermodynamic stability scale and implication for the importance of resonance effect on ylide stabilities

Journal of Organic Chemistry

Volumn 64, Issue 2, 1999, Pages 604-610

  Cheng, Jin Pei ^d   Liu, Bo ^d   Zhao, Yongyu ^a,d   Sun, Yongkai ^d   Zhang, Xian Man ^b,d   Lu, Yun ^c,d  

^a NORTHWESTERN UNIVERSITY   (United States)

^b UTAH STATE UNIVERSITY   (United States)

^c WESLEYAN UNIVERSITY   (United States)

^d NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATION;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION; MOLECULAR INTERACTION; MOLECULAR STABILITY; REACTION ANALYSIS; THERMOSTABILITY;

EID: 0033593486     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981954z     Document Type: Article

References (94)

1. (a) Wittig, G.; Geissler, G. Justus Liebigs Ann Chem. 1953, 580, 44.
2. (b) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
3. (c) Johnson, A. W. Yildes and Imines of Phosphorus; John Wiley & Sons: New York, 1993.
4. (d) Johnson, A. W. Ylide Chemistry; Academic Press: New York, 1966.
5. (e) Cristan, H.-J. Chem. Rev. 1994, 94, 1299.
6. (f) Li. A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341.
7. (g) Hartley, F. R. The Chemistry of Organophosphrous Compounds, Vol. 3; John Wiley & Sons: Chichester, U.K., 1994.
8. For reviews and representative works, see: (a) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. (b) Lloyd, D.; Gorney, I.; Ormiston, R. A. Chem. Soc. Rev. 1987, 16, 45. (c) Rudler, H. R.; Audonin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C., Delgado- Reyas, F. Chem. Soc. Rev. 1991, 20, 503. (d) Huang, Y.-Z. Acc. Chem. Res. 1992, 25, 182. (e) Lloyd, D.; Gosney, I. In The Chemistry of Organic Arsenic, Antimony, and Bismuth Compounds; Patai, S., Ed.; John Wiley & Sons: Chichester, U.K., 1994. (f) Ye, T.; Mekervey, M. A. Chem. Rev. 1994, 94, 1091. (g) Porter, A. E. A. Adv. Heterocycl. Chem. 1989, 45, 151. (h) Krief, A. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; John Wiley & Sons; Chichester, U.K., 1987. (i) Trost, B. M. Sulfer Ylides; Academic Press: New York, 1975.
9. For reviews and representative works, see: (a) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. (b) Lloyd, D.; Gorney, I.; Ormiston, R. A. Chem. Soc. Rev. 1987, 16, 45. (c) Rudler, H. R.; Audonin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C., Delgado- Reyas, F. Chem. Soc. Rev. 1991, 20, 503. (d) Huang, Y.-Z. Acc. Chem. Res. 1992, 25, 182. (e) Lloyd, D.; Gosney, I. In The Chemistry of Organic Arsenic, Antimony, and Bismuth Compounds; Patai, S., Ed.; John Wiley & Sons: Chichester, U.K., 1994. (f) Ye, T.; Mekervey, M. A. Chem. Rev. 1994, 94, 1091. (g) Porter, A. E. A. Adv. Heterocycl. Chem. 1989, 45, 151. (h) Krief, A. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; John Wiley & Sons; Chichester, U.K., 1987. (i) Trost, B. M. Sulfer Ylides; Academic Press: New York, 1975.
10. For reviews and representative works, see: (a) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. (b) Lloyd, D.; Gorney, I.; Ormiston, R. A. Chem. Soc. Rev. 1987, 16, 45. (c) Rudler, H. R.; Audonin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C., Delgado-Reyas, F. Chem. Soc. Rev. 1991, 20, 503. (d) Huang, Y.-Z. Acc. Chem. Res. 1992, 25, 182. (e) Lloyd, D.; Gosney, I. In The Chemistry of Organic Arsenic, Antimony, and Bismuth Compounds; Patai, S., Ed.; John Wiley & Sons: Chichester, U.K., 1994. (f) Ye, T.; Mekervey, M. A. Chem. Rev. 1994, 94, 1091. (g) Porter, A. E. A. Adv. Heterocycl. Chem. 1989, 45, 151. (h) Krief, A. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; John Wiley & Sons; Chichester, U.K., 1987. (i) Trost, B. M. Sulfer Ylides; Academic Press: New York, 1975.
11. For reviews and representative works, see: (a) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. (b) Lloyd, D.; Gorney, I.; Ormiston, R. A. Chem. Soc. Rev. 1987, 16, 45. (c) Rudler, H. R.; Audonin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C., Delgado- Reyas, F. Chem. Soc. Rev. 1991, 20, 503. (d) Huang, Y.-Z. Acc. Chem. Res. 1992, 25, 182. (e) Lloyd, D.; Gosney, I. In The Chemistry of Organic Arsenic, Antimony, and Bismuth Compounds; Patai, S., Ed.; John Wiley & Sons: Chichester, U.K., 1994. (f) Ye, T.; Mekervey, M. A. Chem. Rev. 1994, 94, 1091. (g) Porter, A. E. A. Adv. Heterocycl. Chem. 1989, 45, 151. (h) Krief, A. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; John Wiley & Sons; Chichester, U.K., 1987. (i) Trost, B. M. Sulfer Ylides; Academic Press: New York, 1975.
12. For reviews and representative works, see: (a) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. (b) Lloyd, D.; Gorney, I.; Ormiston, R. A. Chem. Soc. Rev. 1987, 16, 45. (c) Rudler, H. R.; Audonin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C., Delgado- Reyas, F. Chem. Soc. Rev. 1991, 20, 503. (d) Huang, Y.-Z. Acc. Chem. Res. 1992, 25, 182. (e) Lloyd, D.; Gosney, I. In The Chemistry of Organic Arsenic, Antimony, and Bismuth Compounds; Patai, S., Ed.; John Wiley & Sons: Chichester, U.K., 1994. (f) Ye, T.; Mekervey, M. A. Chem. Rev. 1994, 94, 1091. (g) Porter, A. E. A. Adv. Heterocycl. Chem. 1989, 45, 151. (h) Krief, A. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; John Wiley & Sons; Chichester, U.K., 1987. (i) Trost, B. M. Sulfer Ylides; Academic Press: New York, 1975.
13. For reviews and representative works, see: (a) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. (b) Lloyd, D.; Gorney, I.; Ormiston, R. A. Chem. Soc. Rev. 1987, 16, 45. (c) Rudler, H. R.; Audonin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C., Delgado- Reyas, F. Chem. Soc. Rev. 1991, 20, 503. (d) Huang, Y.-Z. Acc. Chem. Res. 1992, 25, 182. (e) Lloyd, D.; Gosney, I. In The Chemistry of Organic Arsenic, Antimony, and Bismuth Compounds; Patai, S., Ed.; John Wiley & Sons: Chichester, U.K., 1994. (f) Ye, T.; Mekervey, M. A. Chem. Rev. 1994, 94, 1091. (g) Porter, A. E. A. Adv. Heterocycl. Chem. 1989, 45, 151. (h) Krief, A. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; John Wiley & Sons; Chichester, U.K., 1987. (i) Trost, B. M. Sulfer Ylides; Academic Press: New York, 1975.
14. For reviews and representative works, see: (a) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. (b) Lloyd, D.; Gorney, I.; Ormiston, R. A. Chem. Soc. Rev. 1987, 16, 45. (c) Rudler, H. R.; Audonin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C., Delgado- Reyas, F. Chem. Soc. Rev. 1991, 20, 503. (d) Huang, Y.-Z. Acc. Chem. Res. 1992, 25, 182. (e) Lloyd, D.; Gosney, I. In The Chemistry of Organic Arsenic, Antimony, and Bismuth Compounds; Patai, S., Ed.; John Wiley & Sons: Chichester, U.K., 1994. (f) Ye, T.; Mekervey, M. A. Chem. Rev. 1994, 94, 1091. (g) Porter, A. E. A. Adv. Heterocycl. Chem. 1989, 45, 151. (h) Krief, A. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; John Wiley & Sons; Chichester, U.K., 1987. (i) Trost, B. M. Sulfer Ylides; Academic Press: New York, 1975.
15. For reviews and representative works, see: (a) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. (b) Lloyd, D.; Gorney, I.; Ormiston, R. A. Chem. Soc. Rev. 1987, 16, 45. (c) Rudler, H. R.; Audonin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C., Delgado- Reyas, F. Chem. Soc. Rev. 1991, 20, 503. (d) Huang, Y.-Z. Acc. Chem. Res. 1992, 25, 182. (e) Lloyd, D.; Gosney, I. In The Chemistry of Organic Arsenic, Antimony, and Bismuth Compounds; Patai, S., Ed.; John Wiley & Sons: Chichester, U.K., 1994. (f) Ye, T.; Mekervey, M. A. Chem. Rev. 1994, 94, 1091. (g) Porter, A. E. A. Adv. Heterocycl. Chem. 1989, 45, 151. (h) Krief, A. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; John Wiley & Sons; Chichester, U.K., 1987. (i) Trost, B. M. Sulfer Ylides; Academic Press: New York, 1975.
16. For reviews and representative works, see: (a) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. (b) Lloyd, D.; Gorney, I.; Ormiston, R. A. Chem. Soc. Rev. 1987, 16, 45. (c) Rudler, H. R.; Audonin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C., Delgado- Reyas, F. Chem. Soc. Rev. 1991, 20, 503. (d) Huang, Y.-Z. Acc. Chem. Res. 1992, 25, 182. (e) Lloyd, D.; Gosney, I. In The Chemistry of Organic Arsenic, Antimony, and Bismuth Compounds; Patai, S., Ed.; John Wiley & Sons: Chichester, U.K., 1994. (f) Ye, T.; Mekervey, M. A. Chem. Rev. 1994, 94, 1091. (g) Porter, A. E. A. Adv. Heterocycl. Chem. 1989, 45, 151. (h) Krief, A. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; John Wiley & Sons; Chichester, U.K., 1987. (i) Trost, B. M. Sulfer Ylides; Academic Press: New York, 1975.
17. For a few examples from numerous works, see: (a) Francl, M. M.; Fellow, R. C.; Allen, L. C. J. Am. Chem. Soc. 1988, 110, 3723. (b) Streiwieser, A., Jr.; Rajca, A.; MeDowell, R. S.; Glaser, R. J. Am. Chem. Soc. 1987, 109, 4184. (c) Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434. (d) Dixon, D. A.; Dunning, T. H., Jr.; Eades, R. A.; Gassman, P. G. J. Am. Chem. Soc. 1983, 105, 7011. (e) Sudhaker, P. V.; Lammertsma, K. J. Am. Chem. Soc. 1991, 113, 1899. (f) Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1987, 109, 1. (g) Naito, T.; Nagase, S.; Yamataka, H. J. Am. Chem. Soc. 1994, 116, 10080. (h) Bachrach, S. M. J. Org. Chem. 1992, 57, 4367. (i) Vedejs, E.; Peterson, M. J. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds; Wiley: New York, 1994; Vol. 4, pp 1-157. (j) Pople, J. A.; Raghavachari, K.; Frisch, M. J.; Binkley, J. S.; Schleyer, P. v. R. J. Am. Chem. Soc. 1983, 105, 6389. (k) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217.
18. For a few examples from numerous works, see: (a) Francl, M. M.; Fellow, R. C.; Allen, L. C. J. Am. Chem. Soc. 1988, 110, 3723. (b) Streiwieser, A., Jr.; Rajca, A.; MeDowell, R. S.; Glaser, R. J. Am. Chem. Soc. 1987, 109, 4184. (c) Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434. (d) Dixon, D. A.; Dunning, T. H., Jr.; Eades, R. A.; Gassman, P. G. J. Am. Chem. Soc. 1983, 105, 7011. (e) Sudhaker, P. V.; Lammertsma, K. J. Am. Chem. Soc. 1991, 113, 1899. (f) Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1987, 109, 1. (g) Naito, T.; Nagase, S.; Yamataka, H. J. Am. Chem. Soc. 1994, 116, 10080. (h) Bachrach, S. M. J. Org. Chem. 1992, 57, 4367. (i) Vedejs, E.; Peterson, M. J. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds; Wiley: New York, 1994; Vol. 4, pp 1-157. (j) Pople, J. A.; Raghavachari, K.; Frisch, M. J.; Binkley, J. S.; Schleyer, P. v. R. J. Am. Chem. Soc. 1983, 105, 6389. (k) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217.
19. For a few examples from numerous works, see: (a) Francl, M. M.; Fellow, R. C.; Allen, L. C. J. Am. Chem. Soc. 1988, 110, 3723. (b) Streiwieser, A., Jr.; Rajca, A.; MeDowell, R. S.; Glaser, R. J. Am. Chem. Soc. 1987, 109, 4184. (c) Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434. (d) Dixon, D. A.; Dunning, T. H., Jr.; Eades, R. A.; Gassman, P. G. J. Am. Chem. Soc. 1983, 105, 7011. (e) Sudhaker, P. V.; Lammertsma, K. J. Am. Chem. Soc. 1991, 113, 1899. (f) Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1987, 109, 1. (g) Naito, T.; Nagase, S.; Yamataka, H. J. Am. Chem. Soc. 1994, 116, 10080. (h) Bachrach, S. M. J. Org. Chem. 1992, 57, 4367. (i) Vedejs, E.; Peterson, M. J. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds; Wiley: New York, 1994; Vol. 4, pp 1-157. (j) Pople, J. A.; Raghavachari, K.; Frisch, M. J.; Binkley, J. S.; Schleyer, P. v. R. J. Am. Chem. Soc. 1983, 105, 6389. (k) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217.
20. For a few examples from numerous works, see: (a) Francl, M. M.; Fellow, R. C.; Allen, L. C. J. Am. Chem. Soc. 1988, 110, 3723. (b) Streiwieser, A., Jr.; Rajca, A.; MeDowell, R. S.; Glaser, R. J. Am. Chem. Soc. 1987, 109, 4184. (c) Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434. (d) Dixon, D. A.; Dunning, T. H., Jr.; Eades, R. A.; Gassman, P. G. J. Am. Chem. Soc. 1983, 105, 7011. (e) Sudhaker, P. V.; Lammertsma, K. J. Am. Chem. Soc. 1991, 113, 1899. (f) Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1987, 109, 1. (g) Naito, T.; Nagase, S.; Yamataka, H. J. Am. Chem. Soc. 1994, 116, 10080. (h) Bachrach, S. M. J. Org. Chem. 1992, 57, 4367. (i) Vedejs, E.; Peterson, M. J. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds; Wiley: New York, 1994; Vol. 4, pp 1-157. (j) Pople, J. A.; Raghavachari, K.; Frisch, M. J.; Binkley, J. S.; Schleyer, P. v. R. J. Am. Chem. Soc. 1983, 105, 6389. (k) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217.
21. For a few examples from numerous works, see: (a) Francl, M. M.; Fellow, R. C.; Allen, L. C. J. Am. Chem. Soc. 1988, 110, 3723. (b) Streiwieser, A., Jr.; Rajca, A.; MeDowell, R. S.; Glaser, R. J. Am. Chem. Soc. 1987, 109, 4184. (c) Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434. (d) Dixon, D. A.; Dunning, T. H., Jr.; Eades, R. A.; Gassman, P. G. J. Am. Chem. Soc. 1983, 105, 7011. (e) Sudhaker, P. V.; Lammertsma, K. J. Am. Chem. Soc. 1991, 113, 1899. (f) Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1987, 109, 1. (g) Naito, T.; Nagase, S.; Yamataka, H. J. Am. Chem. Soc. 1994, 116, 10080. (h) Bachrach, S. M. J. Org. Chem. 1992, 57, 4367. (i) Vedejs, E.; Peterson, M. J. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds; Wiley: New York, 1994; Vol. 4, pp 1-157. (j) Pople, J. A.; Raghavachari, K.; Frisch, M. J.; Binkley, J. S.; Schleyer, P. v. R. J. Am. Chem. Soc. 1983, 105, 6389. (k) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217.
22. For a few examples from numerous works, see: (a) Francl, M. M.; Fellow, R. C.; Allen, L. C. J. Am. Chem. Soc. 1988, 110, 3723. (b) Streiwieser, A., Jr.; Rajca, A.; MeDowell, R. S.; Glaser, R. J. Am. Chem. Soc. 1987, 109, 4184. (c) Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434. (d) Dixon, D. A.; Dunning, T. H., Jr.; Eades, R. A.; Gassman, P. G. J. Am. Chem. Soc. 1983, 105, 7011. (e) Sudhaker, P. V.; Lammertsma, K. J. Am. Chem. Soc. 1991, 113, 1899. (f) Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1987, 109, 1. (g) Naito, T.; Nagase, S.; Yamataka, H. J. Am. Chem. Soc. 1994, 116, 10080. (h) Bachrach, S. M. J. Org. Chem. 1992, 57, 4367. (i) Vedejs, E.; Peterson, M. J. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds; Wiley: New York, 1994; Vol. 4, pp 1-157. (j) Pople, J. A.; Raghavachari, K.; Frisch, M. J.; Binkley, J. S.; Schleyer, P. v. R. J. Am. Chem. Soc. 1983, 105, 6389. (k) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217.
23. For a few examples from numerous works, see: (a) Francl, M. M.; Fellow, R. C.; Allen, L. C. J. Am. Chem. Soc. 1988, 110, 3723. (b) Streiwieser, A., Jr.; Rajca, A.; MeDowell, R. S.; Glaser, R. J. Am. Chem. Soc. 1987, 109, 4184. (c) Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434. (d) Dixon, D. A.; Dunning, T. H., Jr.; Eades, R. A.; Gassman, P. G. J. Am. Chem. Soc. 1983, 105, 7011. (e) Sudhaker, P. V.; Lammertsma, K. J. Am. Chem. Soc. 1991, 113, 1899. (f) Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1987, 109, 1. (g) Naito, T.; Nagase, S.; Yamataka, H. J. Am. Chem. Soc. 1994, 116, 10080. (h) Bachrach, S. M. J. Org. Chem. 1992, 57, 4367. (i) Vedejs, E.; Peterson, M. J. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds; Wiley: New York, 1994; Vol. 4, pp 1-157. (j) Pople, J. A.; Raghavachari, K.; Frisch, M. J.; Binkley, J. S.; Schleyer, P. v. R. J. Am. Chem. Soc. 1983, 105, 6389. (k) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217.
24. For a few examples from numerous works, see: (a) Francl, M. M.; Fellow, R. C.; Allen, L. C. J. Am. Chem. Soc. 1988, 110, 3723. (b) Streiwieser, A., Jr.; Rajca, A.; MeDowell, R. S.; Glaser, R. J. Am. Chem. Soc. 1987, 109, 4184. (c) Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434. (d) Dixon, D. A.; Dunning, T. H., Jr.; Eades, R. A.; Gassman, P. G. J. Am. Chem. Soc. 1983, 105, 7011. (e) Sudhaker, P. V.; Lammertsma, K. J. Am. Chem. Soc. 1991, 113, 1899. (f) Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1987, 109, 1. (g) Naito, T.; Nagase, S.; Yamataka, H. J. Am. Chem. Soc. 1994, 116, 10080. (h) Bachrach, S. M. J. Org. Chem. 1992, 57, 4367. (i) Vedejs, E.; Peterson, M. J. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds; Wiley: New York, 1994; Vol. 4, pp 1-157. (j) Pople, J. A.; Raghavachari, K.; Frisch, M. J.; Binkley, J. S.; Schleyer, P. v. R. J. Am. Chem. Soc. 1983, 105, 6389. (k) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217.
25. For a few examples from numerous works, see: (a) Francl, M. M.; Fellow, R. C.; Allen, L. C. J. Am. Chem. Soc. 1988, 110, 3723. (b) Streiwieser, A., Jr.; Rajca, A.; MeDowell, R. S.; Glaser, R. J. Am. Chem. Soc. 1987, 109, 4184. (c) Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434. (d) Dixon, D. A.; Dunning, T. H., Jr.; Eades, R. A.; Gassman, P. G. J. Am. Chem. Soc. 1983, 105, 7011. (e) Sudhaker, P. V.; Lammertsma, K. J. Am. Chem. Soc. 1991, 113, 1899. (f) Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1987, 109, 1. (g) Naito, T.; Nagase, S.; Yamataka, H. J. Am. Chem. Soc. 1994, 116, 10080. (h) Bachrach, S. M. J. Org. Chem. 1992, 57, 4367. (i) Vedejs, E.; Peterson, M. J. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds; Wiley: New York, 1994; Vol. 4, pp 1-157. (j) Pople, J. A.; Raghavachari, K.; Frisch, M. J.; Binkley, J. S.; Schleyer, P. v. R. J. Am. Chem. Soc. 1983, 105, 6389. (k) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217.
26. For a few examples from numerous works, see: (a) Francl, M. M.; Fellow, R. C.; Allen, L. C. J. Am. Chem. Soc. 1988, 110, 3723. (b) Streiwieser, A., Jr.; Rajca, A.; MeDowell, R. S.; Glaser, R. J. Am. Chem. Soc. 1987, 109, 4184. (c) Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434. (d) Dixon, D. A.; Dunning, T. H., Jr.; Eades, R. A.; Gassman, P. G. J. Am. Chem. Soc. 1983, 105, 7011. (e) Sudhaker, P. V.; Lammertsma, K. J. Am. Chem. Soc. 1991, 113, 1899. (f) Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1987, 109, 1. (g) Naito, T.; Nagase, S.; Yamataka, H. J. Am. Chem. Soc. 1994, 116, 10080. (h) Bachrach, S. M. J. Org. Chem. 1992, 57, 4367. (i) Vedejs, E.; Peterson, M. J. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds; Wiley: New York, 1994; Vol. 4, pp 1-157. (j) Pople, J. A.; Raghavachari, K.; Frisch, M. J.; Binkley, J. S.; Schleyer, P. v. R. J. Am. Chem. Soc. 1983, 105, 6389. (k) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217.
27. For a few examples from numerous works, see: (a) Francl, M. M.; Fellow, R. C.; Allen, L. C. J. Am. Chem. Soc. 1988, 110, 3723. (b) Streiwieser, A., Jr.; Rajca, A.; MeDowell, R. S.; Glaser, R. J. Am. Chem. Soc. 1987, 109, 4184. (c) Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434. (d) Dixon, D. A.; Dunning, T. H., Jr.; Eades, R. A.; Gassman, P. G. J. Am. Chem. Soc. 1983, 105, 7011. (e) Sudhaker, P. V.; Lammertsma, K. J. Am. Chem. Soc. 1991, 113, 1899. (f) Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1987, 109, 1. (g) Naito, T.; Nagase, S.; Yamataka, H. J. Am. Chem. Soc. 1994, 116, 10080. (h) Bachrach, S. M. J. Org. Chem. 1992, 57, 4367. (i) Vedejs, E.; Peterson, M. J. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds; Wiley: New York, 1994; Vol. 4, pp 1-157. (j) Pople, J. A.; Raghavachari, K.; Frisch, M. J.; Binkley, J. S.; Schleyer, P. v. R. J. Am. Chem. Soc. 1983, 105, 6389. (k) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217.
28. (a) Bestmann, H. J. Chem. Ber. 1962, 95, 58.
29. (b) Johnson, A. W.; Lee, S. Y.; Swor, R. A.; Royer, L. D. J. Am. Chem. Soc. 1966, 88, 1953.
30. (c) Fliszar, S.; Hudson, R. F.; Salvadori, G. Helv. Chim. Acta 1963, 46, 1580.
31. (d) Speziale, A. J.; Ratts, K. W. J. Am. Chem. Soc. 1963, 85, 2790.
32. (e) Issleib, K.; Linder, R. Liebigs Ann. Chem. 1967, 707, 120.
33. (f) Johnson, A. W.; Ronald, T. A. Can. J. Chem. 1968, 46, 461.
34. (g) Johnson, A. W.; LaCount, R. B. Tetrahedron 1960, 9, 130.
35. (h) Gunnar, A.; Songstad, J. Acta Chem. Scand. 1964, 18, 655.
36. (i) Edwards, J. O.; Pearson, R. G. J. Am. Chem. Soc. 1962, 84, 16.
37. (j) Phillips, W. G.; Ratts, K. W. J. Org. Chem. 1970, 35, 3144.
38. (a) Bordwell, F. G. Acc. Chem. Chem. 1988, 21, 456 and references therein.
39. (b) Bausch, M. J.; Gong, Y. J. Am. Chem. Soc. 1994, 116, 5963.
40. (a) Bordwell, F. G.; Bausch, M. J. J. Am. Chem. Soc. 1986, 108, 1979.
41. (b) Bordwell, F. G.; Cheng, J.-P.; Harrelson, J. A., Jr. J. Am. Chem. Soc. 1988, 110, 1229.
42. (c) Bordwell, F. G.; Cheng, J.-P.; Bausch, M. J. J. Am. Chem. Soc. 1988, 110, 2867, 2872.
43. (d) Bordwell, F. G.; Cheng, J.-P. J. Am. Chem. Soc. 1989, 111, 1792.
44. (e) Bordwell, F. G.; Cheng, J.-P. J. Am. Chem. Soc. 1991, 113, 1736.
45. (f) Bordwell, F. G.; Cheng, J.-P.; Ji, G.; Satish, A. V.; Zhang, X. J. Am. Chem. Soc. 1991, 113, 9790.
46. (g) Zhang, X.-M.; Bordwell, F. G. J. Am. Chem. Soc. 1992, 114, 9787.
47. (h) Bordwell, F. G.; Zhang, X.-M.; Cheng, J.-P. J. Am. Chem. Soc. 1994, 116, 6605.
48. (i) Bordwell, F. G.; Zhang, S. J. Am. Chem. Soc. 1995, 117, 4858.
49. (a) Zhang, X.-M.; Bordwell, F. G.; Puy, M. V. D.; Fried, H. E. J. Org. Chem. 1993, 58, 3060.
50. (b) Zhang, X.-M.; Bordwell, F. G. J. Am. Chem. Soc. 1994, 116, 968.
51. (a) Cheng, J.-P.; Liu, B.; Zhao, Y.; Zhang, X.-M. J. Org. Chem. 1998, 63, 7072.
52. (b) Cheng, J.-P.; Liu, B.; Zhang, X.-M. J. Org Chem. 1998, 63, 7574.
53. (c) Cheng, J.-P.; Lu, Y.; Zhu, X.; Mu, J. J. Org. Chem. 1998, 63, 6108.
54. (d) Cheng, J.-P.; Xian, M.; Wang, K.; Zhu, X.; Yin, Z.; Wang, P. G. J. Am. Chem. Soc. 1998, 120, 10266.
55. (e) Zhao, Y.; Bordwell, F. G.; Cheng, J.-P.; Wang, D. J. Am. Chem. Soc. 1997, 119, 9125.
56. (f) Zhao, Y. Ph.D. Dissertation, Nankai University, Tianjin, China, 1994.
57. (g) Cheng, J.-P.; Zhao, Y. Tetrahedron 1993, 49, 5267.
58. (h) Cheng, J.-P.; Zhao, Y.; Huan, Z. Sci. China (Ser. B) (Engl.) 1995, 38, 1417.
59. (i) Cheng, J.-P.; Zheng, Z. Tetrahedron Lett. 1996, 37, 1457.
60. (j) Cheng, J.-P.; Wang, K.; Yin, Z.; Zhu, X.; Lu, Y. Tetrahedron Lett. 1998, 39, 7925.
61. (k) Cheng, J.-P.; Lu, Y.; Liu, B.; Zhao, Y.; Wang, D.; Sun, Y.; Mi, J. Sci. China (Ser. B) (Engl.) 1998, 41, 215.
62. (l) Cheng, J.-P.; Lu, Y. J. Phys. Org. Chem. 1997, 10, 577.
63. (m) Liu, B.; Huan, Z.; Cheng, J.-P. Acta Chim. Sin. 1997, 55, 123.
64. Kutzelnigg, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 272.
65. (a) March, J. Advanced Organic Chemistry, 4th ed.; John Wiley & Sons: New York, 1992.
66. (b) Hoffman, R. V. Organic Chemistry; Oxford University Press: New York, 1997.
67. (a) Steiner, E. C.; Gilbert, J. M. J. Am. Chem. Soc. 1963, 85, 3054.
68. (b) Kolfhoff, I. M.; Chantooni, J. K., Jr.; Bhowmik, S. J. Am. Chem. Soc. 1968, 90, 23.
69. (c) Ritchie, C. D. Solute-Solvent Interactions; Coetzee, J. F., Ritchie, C. D., Eds.; Marcel Dekker: New York, 1969, Chapter 4.
70. Izutsu, K. Acid-Base Dissociation Constants in Dipolar Aprotic Solvents, IUPAC Chem. Data Ser. No. 35; Blackwell Scientific Publications: Oxford, 1990.
71. Taft, R. W.; Bordwell, F. G. Acc. Chem. Res. 1988, 21, 463.
72. Mansch, C.; Leo, A.; Taft, T. W. Chem. Rev. 1991, 91, 165.
73. For a more detailed discussion on this issue, see ref 7b and the quoted references therein. More discussions could be found in refs 1c, 3a,b,d,e,g-j, and 16.
74. (a) Shimizu, T.; Matsuhisa, A.; Kamigata, N.; Ikuta, S. J. Chem. Soc., Perkin Trans. 2 1995, 1805.
75. (b) Vourinen, E.; Chalmers, A. A.; Dillen, J. L. M.; Modro, T. A. Tetrahedron 1991, 47, 8611.
76. McDowell, R. S.; Streiwieser, A., Jr. J. Am. Chem. Soc. 1985, 107, 5849.
77. The dipole polarizability of ∼35 for Te is a rough estimate based on comparisons with the relevant values listed in ref 9.
78. (a) Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry, 5th ed.; Wiley: New York, 1988.
79. (b) Wells, A. F. Structural Inorganic Chemistry, 5th ed.; Clarendon: Oxford, 1984.
80. (c) Angyan, J. G.; Poirier, P. A.; Kucsman, A.; Csizmedia, I. G. J. Am. Chem. Soc. 1987, 109, 2237.
81. (d) Maouche, Y.; Brianso, M. C.; Maouche, B. THEOCHEM 1988, 166, 449.
82. Geoffroy, M.; Rao, G.; Tancic, Z.; Bernardinelli, G. J. Am. Chem. Soc. 1990, 112, 2826.
83. 3f,22
84. (a) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 867.
85. (b) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353.
86. (c) Johnson, A. W.; Lacount, R. B. J. Am. Chem. Soc. 1961, 83, 417.
87. +-substituted series was not intended here because it is not structurally comparable with all others for not having functionable d-orbitals and the points in correlation are also too limited (n = 3) for the correlation data to be highly reliable.
88. McDonald, R. N.; Campbell, T. W. J. Org. Chem. 1959, 24, 1969.
89. Tsvetkov, E. N.; Bondarenko, N. A.; Malakhova, I. G.; Kabachnik, M. I. Synthesis 1986, 3, 198.
90. Mesyats, S. P.; Tsvetkov, E. N.; Petrov, E. S.; Shelganova, N. N.; Shcherbina, T. M.; Schatenshtein, A. I.; Kabachnilz, M. I. Iza. Akad. Nauk SSSR, Ser, Khim. 1974, 11, 2497.
91. Zhong, Q.; Shao, J.; Liu, C. Synth. Commun. 1991, 21, 869.
92. Johnson, A. W. J. Org. Chem. 1960, 25, 183.
93. Mathews, W. S.; Bares, J. E.; Bartmess, J. E.; Bordwell, F. G.; Cornforth, F. J.; Drucker, G. E.; Margolin, Z.; McCallum, R. J.; McCollum, G. J.; Vanier, N. R. J. Am. Chem. Soc. 1975, 97, 7006.
94. Anions in this series are less stable. Therefore a quick three-point titration was made and the titration manner was followed as close to each other as possible in order to minimize the systematic error within the family. Larger standard deviation is still obvious as the result of the low anion stability.