π4s + π2s cycloadditions: Allyl anions plus ethylene

Tetrahedron Letters

Volumn 37, Issue 43, 1996, Pages 7679-7682

  Sauers, Ronald R ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE DERIVATIVE;

ARTICLE; CALCULATION; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR DYNAMICS; THEORY;

EID: 0030597091     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01756-X     Document Type: Article

References (20)

1. 1. (a) Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem. Int. Ed. Eng. 1992, 31, 682-708.
2. (b) Houk, K. N.; Gonzalez, J.; Li, Y. Acc. Chem. Res. 1995, 28, 81-89.
3. (c) Bach, R. D.; McDouall, J. J. W.; Schlegel, H. B. J. Org. Chem. 1989, 54, 2931-2395.
4. (d) Jorgensen, W. L.; Lim, D.; Blake, J. F. J. Am. Chem. Soc. 1993, 115, 2936-2942.
5. (e) Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1993, 115, 7478-7485.
6. (f) Borden, W. T.; Davidson, E. R. Acc. Chem. Res. 1996, 29, 67-75.
7. 2. Carruthers, W. "Cycloaddition Reactions in Organic Synthesis" Pergamon, New York, 1990, p 209ff.
8. 3. (a) Marino, J. P.; Mesbergen, W. B. J. Am. Chem. Soc. 1974, 96, 4050-4052.
9. (b) Eidenschink, A.; Kauffmann, T. Angew. Chem. Int. Ed. Eng. 1972, 11, 292-3.
10. (c) Kauffmann, T. Angew. Chem. Int. Ed. Eng. 1974, 13, 627.
11. (d) Nibbering, N. M. M. in "Kinetics of Ion-Molecule Reactions," P. Ausloos, ed., Plenum, New York 1979, p. 165.
12. 4. de Pascual-Teresa, B.; Houk, K. N. Tetrahedron Letters 1996, 37, 1759-1762.
13. 5. (a) Sauers, R. R. Tetrahedron Letters 1994, 35, 7213-7216.
14. (b) Sauers, R. R. Tetrahedron Letters 1996, 37, 149-152.
15. 6. All optimations utilized Gaussian94 Revision B.1 using default convergence criteria: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; 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-Gorden, M.; Gonzalez, C., and Pople, J. A.; Gaussian, Inc.; Pittsburgh PA; 1995. Frequencies are unscaled.
16. 7. Eigenvalues at the MP2(FC)/6-311+G(d) level are: π (-0.37441); χ1 (-0.19717); χ2 (-0.01530). Eigenvalues at the MP2(FC)/6-311++G(d) level are: π (-0.37436); χ1 (-0.19580); χ2 (-0.01926).
17. 8. Townshend, R. E.; Ramunni, G.; Segal, G.; Hehre, W. J.; Salem, L. J. Am. Chem. Soc. 1976, 98, 2190-2198.
18. 9. Hommes, N. J.v. E.; Buhl, M.; Schleyer, P. v. R. J. Organomet. Chem. 1991, 409, 307-320.
19. 10. Wiberg, K. B.; Breneman, C.M.; LePage, T. J. J. Am. Chem. Soc. 1990, 112, 61-72.
20. 11. HOMO representation prepared from Spartan, v 4.0: Wavefunction, Inc., Irvine, CA 92715.