Mechanism of the Chemoselective and Stereoselective Ring Opening of Oxathiaphospholanes: An Ab Initio Study

Journal of Organic Chemistry

Volumn 62, Issue 17, 1997, Pages 5793-5800

  Uchimaru, Tadafumi ^a   Stec, Wojciech J ^c   Taira, Kazunari ^b  

^a NATL INST OF MAT AND CHEM RES   (Japan)

^b UNIVERSITY OF TSUKUBA   (Japan)

^c CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001700991     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962220u     Document Type: Article

References (40)

1. Stec, W. J.; Grajkowski, A.; Koziolkiewicz, M.; Uznanski, B. Nucleic Acids Res. 1991, 19, 5883-5888.
2. Uznanski, B.; Grajkowski, A.; Krzyzanowska, B.; Kazmierkowska, A.; Stec, W. J.; Wieczorek, M. W.; Blaszczyk, J. J. Am. Chem. Soc. 1992, 114, 10197-10202.
3. Stec, W. J.; Grajkowski, A.; Kobylanska, A.; Karwowski, B.; Koziolkiewicz, M.; Misiura, K.; Okruszek, A.; Wilk, A.; Guga, P.; Boczkowska, M. J. Am. Chem. Soc. 1995, 117, 12019-12029.
4. Westheimer, F. H. Acc. Chem. Res. 1968, 1, 70-78.
5. Thatcher, G. R. J.; Kluger, R. Adv. Phys. Org. Chem. 1989, 25, 99-265.
6. Berry, R. S. J. Chem. Phys. 1960, 32, 933-938.
7. Mislow, K. Acc. Chem. Res. 1970, 3, 321-331.
8. An alternative turnstile process has been proposed; see: Ugi, I.; Marquarding, D.; Klusacek, H.; Gillespie, P.; Ramirez, F. Acc. Chem. Res. 1971, 4, 288-296. Experimental results have generally been interpreted in terms of the Berry process: Russegger, P.; Brickmann, J. Chem. Phys. Lett. 1975, 30, 276-278.
9. An alternative turnstile process has been proposed; see: Ugi, I.; Marquarding, D.; Klusacek, H.; Gillespie, P.; Ramirez, F. Acc. Chem. Res. 1971, 4, 288-296. Experimental results have generally been interpreted in terms of the Berry process: Russegger, P.; Brickmann, J. Chem. Phys. Lett. 1975, 30, 276-278.
10. Holmes, R. R. J. Am. Chem. Soc. 1978, 100, 433-446.
11. Deiters, J. A.; Holmes, R. R.; Holmes, J. M. J. Am. Chem. Soc. 1988, 110, 7672-7681.
12. Hoffmann, R.; Howell, J. M.; Mutterties, E. L. J. Am. Chem. Soc. 1972, 94, 3047-3058.
13. Strich, A.; Veliiard, A. J. Am. Chem. Soc. 1973, 95, 5574-5581.
14. McDowell, R. S.; Streitwieser, A., Jr. J. Am. Chem. Soc. 1985, 107, 5849-5855.
15. Wang, P.; Zhang, Y.; Glasser, R.; Reed, A. E.; Schleyer, P. v. R.; Streitwieser, A. J. Am. Chem. Soc. 1991, 113, 55-64.
16. Lim, C.; Tole, P. J. Phys. Chem. 1992, 96, 5217-5219.
17. Tole, P.; Lim, C. J. Phys. Chem. 1993, 97, 6212-6219.
18. Tole, P.; Lim, C. J. Am. Chem. Soc. 1994, 116, 3922-3931.
19. Cameron, D. R.; Thatcher, G. R. J. J. Org. Chem. 1996, 61, 5986-5997.
20. Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92; Gaussian, Inc.: Pittsburgh, PA, 1992.
21. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94; Gaussian, Inc.: Pittsburgh, PA, 1995.
22. Carpenter, J. E.; Hehre, W. J.; Kahn, S. D. Spartan version 4.0; Wavefunction Inc.: Irvine, CA.
23. Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211-7218.
24. Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 4066-4073.
25. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-746.
26. Carpenter, J. E.; Weinhold, F. THEOCHEM 1988, 269, 41-62.
27. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
28. Reed, A. E.; Schleyer, P. v. R. Inorg. Chem. 1988, 27, 3969-3987.
29. Dejaegere, A.; Karplus, M. J. Am. Chem. Soc. 1993, 115, 5316-5317.
30. Dejaegere, A.; Liang, X.; Karplus, M. J. Chem. Soc. Faraday Trans. 1994, 90, 1763-1770.
31. Wong, M. W.; Frisch, M. J.; Wiberg, K. B. J. Am. Chem. Soc. 1991, 113, 4776-4782.
32. Wong, M. W.; Wiberg, K. B.; Frisch, M. J. J. Am. Chem. Soc. 1992, 114, 523-529
33. Wong, M. W.; Wiberg, K. B.; Frisch, M. J. J. Am. Chem. Soc. 1992, 114, 1645-1652.
34. Cieplak, A. S.; Wiberg, K. B. J. Am. Chem. Soc. 1992, 114, 9226-9227.
35. Wong, M. W.; Wiberg, K. B.; Frisch, M. J. J. Comput. Chem. 1995, 16, 385-394.
36. CCDC, University Chemical Laboratory, Cambridge, U.K.
37. The largest deviations in the endocyclic bond lengths and bond angles are 0.037 Å (S-C bond) and 6.1° (bond angle about P-O-C), respectively. The deviations in the exocyclic P-S and P-N bond lengths are less than 0.01 Å.
38. elim-O, with breaking O-C and S-C bonds 0.108 and 0.111 Å longer than the corresponding gas-phase geometries. Conversely, the forming C-S and C-O bonds are 0.064 and 0.053 Å shorter in the solution phase.
39. Wang, P.; Agrafiotis, D. K.; Streitwieser, A.; Schleyer, P. v. R. J. Chem. Soc., Chem. Commun. 1990, 201-203.
40. Wasada, H.; Horao, K. J. Am. Chem. Soc. 1992, 114, 16-27.