Ab initio theoretical studies on the ring-opening modes of the oxiranyl-, aziridinyl-, oxaziridinyl-, and thiaranylmethyl radical systems

Journal of Organic Chemistry

Volumn 61, Issue 1, 1996, Pages 252-256

  Pasto, Daniel J ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000904802     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9505942     Document Type: Article

References (20)

1. Krosley, K W.; Gleicher, G. J.; Clapp, G. E. J. Org. Chem. 1992, 57, 840. Rawqal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. Johns, A.; Murphy, J. Tetrahedron Lett. 1998, 29, 837. Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem Soc., Perkin Trans. 1 1981, 2363. Russell, G. A.; Shi, B. Z. Talk No. 98, Division of Organic Chemistry, National American Chemical Society Meeting, Denver, CO, 1993. Murphy, J. A., Patterson, C. W.; Wooster, N. F. J Chem. Soc , Chem. Commun. 1988, 294. Carlson, R. G.; Huber, J H.-A.; Henton, D. E. J. Chem. Soc., Chem. Commun. 1973, 223.
2. Krosley, K W.; Gleicher, G. J.; Clapp, G. E. J. Org. Chem. 1992, 57, 840. Rawqal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. Johns, A.; Murphy, J. Tetrahedron Lett. 1998, 29, 837. Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem Soc., Perkin Trans. 1 1981, 2363. Russell, G. A.; Shi, B. Z. Talk No. 98, Division of Organic Chemistry, National American Chemical Society Meeting, Denver, CO, 1993. Murphy, J. A., Patterson, C. W.; Wooster, N. F. J Chem. Soc , Chem. Commun. 1988, 294. Carlson, R. G.; Huber, J H.-A.; Henton, D. E. J. Chem. Soc., Chem. Commun. 1973, 223.
3. Krosley, K W.; Gleicher, G. J.; Clapp, G. E. J. Org. Chem. 1992, 57, 840. Rawqal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. Johns, A.; Murphy, J. Tetrahedron Lett. 1998, 29, 837. Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem Soc., Perkin Trans. 1 1981, 2363. Russell, G. A.; Shi, B. Z. Talk No. 98, Division of Organic Chemistry, National American Chemical Society Meeting, Denver, CO, 1993. Murphy, J. A., Patterson, C. W.; Wooster, N. F. J Chem. Soc , Chem. Commun. 1988, 294. Carlson, R. G.; Huber, J H.-A.; Henton, D. E. J. Chem. Soc., Chem. Commun. 1973, 223.
4. Krosley, K W.; Gleicher, G. J.; Clapp, G. E. J. Org. Chem. 1992, 57, 840. Rawqal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. Johns, A.; Murphy, J. Tetrahedron Lett. 1998, 29, 837. Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem Soc., Perkin Trans. 1 1981, 2363. Russell, G. A.; Shi, B. Z. Talk No. 98, Division of Organic Chemistry, National American Chemical Society Meeting, Denver, CO, 1993. Murphy, J. A., Patterson, C. W.; Wooster, N. F. J Chem. Soc , Chem. Commun. 1988, 294. Carlson, R. G.; Huber, J H.-A.; Henton, D. E. J. Chem. Soc., Chem. Commun. 1973, 223.
5. Krosley, K W.; Gleicher, G. J.; Clapp, G. E. J. Org. Chem. 1992, 57, 840. Rawqal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. Johns, A.; Murphy, J. Tetrahedron Lett. 1998, 29, 837. Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem Soc., Perkin Trans. 1 1981, 2363. Russell, G. A.; Shi, B. Z. Talk No. 98, Division of Organic Chemistry, National American Chemical Society Meeting, Denver, CO, 1993. Murphy, J. A., Patterson, C. W.; Wooster, N. F. J Chem. Soc , Chem. Commun. 1988, 294. Carlson, R. G.; Huber, J H.-A.; Henton, D. E. J. Chem. Soc., Chem. Commun. 1973, 223.
6. Krosley, K W.; Gleicher, G. J.; Clapp, G. E. J. Org. Chem. 1992, 57, 840. Rawqal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. Johns, A.; Murphy, J. Tetrahedron Lett. 1998, 29, 837. Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem Soc., Perkin Trans. 1 1981, 2363. Russell, G. A.; Shi, B. Z. Talk No. 98, Division of Organic Chemistry, National American Chemical Society Meeting, Denver, CO, 1993. Murphy, J. A., Patterson, C. W.; Wooster, N. F. J Chem. Soc , Chem. Commun. 1988, 294. Carlson, R. G.; Huber, J H.-A.; Henton, D. E. J. Chem. Soc., Chem. Commun. 1973, 223.
7. Krosley, K W.; Gleicher, G. J.; Clapp, G. E. J. Org. Chem. 1992, 57, 840. Rawqal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. Johns, A.; Murphy, J. Tetrahedron Lett. 1998, 29, 837. Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem Soc., Perkin Trans. 1 1981, 2363. Russell, G. A.; Shi, B. Z. Talk No. 98, Division of Organic Chemistry, National American Chemical Society Meeting, Denver, CO, 1993. Murphy, J. A., Patterson, C. W.; Wooster, N. F. J Chem. Soc , Chem. Commun. 1988, 294. Carlson, R. G.; Huber, J H.-A.; Henton, D. E. J. Chem. Soc., Chem. Commun. 1973, 223.
8. Cook, M.; Hares, O.; Johns, A.; Murphy, J. A.; Patterson, C. W. J. Chem., Soc., Chem. Commun. 1986, 1419. Strogryn, E. L.; Gianni, M. H. Tetrahedron Lett. 1970, 3025.
9. Cook, M.; Hares, O.; Johns, A.; Murphy, J. A.; Patterson, C. W. J. Chem., Soc., Chem. Commun. 1986, 1419. Strogryn, E. L.; Gianni, M. H. Tetrahedron Lett. 1970, 3025.
10. Laurie, D.; Nonhebel, D C.; Suckling, C. J.; Walton, J. C. Tetrahedron 1993, 49, 5869.
11. Krosley, K. W.; Gleicher, G. J. J. Phys. Org. Chem. 1993, 6, 228.
12. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687.
13. Pasto, D. J.; Cottard, F.; Picconatto, C. J. Org. Chem. 1994, 59, 7172.
14. Iodoepoxides have, however, been observed to be formed in the decomposition of allyl hypoiodites (Galatsis, P.; Millan, S. D. Tetrahedron Lett. 1991, 32, 7493. Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. Suginome, H., Wang, J. B.; J. Chem. Soc., Chem. Commun. 1990, 1629.).
15. Iodoepoxides have, however, been observed to be formed in the decomposition of allyl hypoiodites (Galatsis, P.; Millan, S. D. Tetrahedron Lett. 1991, 32, 7493. Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. Suginome, H., Wang, J. B.; J. Chem. Soc., Chem. Commun. 1990, 1629.).
16. Iodoepoxides have, however, been observed to be formed in the decomposition of allyl hypoiodites (Galatsis, P.; Millan, S. D. Tetrahedron Lett. 1991, 32, 7493. Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. Suginome, H., Wang, J. B.; J. Chem. Soc., Chem. Commun. 1990, 1629.).
17. Pasto, D. J.; Krasnansky, R.; Zercher, C. J. Org. Chem. 1987, 52, 3062.
18. The calculations were carried out using the GAUSIAN 92 package of programs (Gaussian 92, Revision G.2, 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, K. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1992.).
19. No attempts have been made to optimize the six π-electron structures.
20. Quenemoen, K.; Borden, W. T.; Davidson, E. R.; Feller, D. J. Am. Chem. Soc 1985, 107, 5054.