Ab initio theoretical study of metallo-dehydrogenation and nucleophilic addition of methyllithium and methylpotassium with crotonaldehyde dimethyl acetal

Tetrahedron

Volumn 53, Issue 23, 1997, Pages 7937-7946

  Fossey, Jacques ^a   Ghigo, Giovanni ^b   Tonachini, Glauco ^b   Venturello, Paolo ^b  

^a ECOLE POLYTECHNIQUE   (France)

^b UNIVERSITY OF TURIN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; MOLECULAR DYNAMICS; PRIORITY JOURNAL; REACTION ANALYSIS; THEORETICAL STUDY;

EID: 84962419790     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00467-5     Document Type: Article

References (37)

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2. D) in metalation of toluene and benzene by BuLi / BuOK base and BuK confirm different behavior of the two: Schlosser, M.; Choi, I. H.; Takagishi, S. Tetrahedron , 1990, 46, 5633-5648.
3. D) in metalation of toluene and benzene by BuLi / BuOK base and BuK confirm different behavior of the two: Schlosser, M.; Choi, I. H.; Takagishi, S. Tetrahedron , 1990, 46, 5633-5648.
4. D) in metalation of toluene and benzene by BuLi / BuOK base and BuK confirm different behavior of the two: Schlosser, M.; Choi, I. H.; Takagishi, S. Tetrahedron , 1990, 46, 5633-5648.
5. D) in metalation of toluene and benzene by BuLi / BuOK base and BuK confirm different behavior of the two: Schlosser, M.; Choi, I. H.; Takagishi, S. Tetrahedron , 1990, 46, 5633-5648.
6. D) in metalation of toluene and benzene by BuLi / BuOK base and BuK confirm different behavior of the two: Schlosser, M.; Choi, I. H.; Takagishi, S. Tetrahedron , 1990, 46, 5633-5648.
7. (a) Effective substituents are for instance: second row elements like sulfur; carbonyl or cyano groups; other conjugated multiple bonds (Michael-type reactions). Also alkenes with an electron donor group in a suitable position (as allylic alcohol, see below) have been reported to readily undergo addition of organolithium. (formula presented) See: Crandall, J. K.; Rojas, A. J. Org. Synth. 1976, 55, 1-3.
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12. (d) Nakamura, M.; Nakamura, E.; Koga, N.; Morokuma, K. J. Chem. Soc., Faraday Trans. 1994, 90, 1789-1798. Nakamura, E.; Nakamura, M.; Miyachi, Y.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1993, 115, 99-106. Nakamura, E.; Miyachi, Y.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 6686-6692.
13. Bailey, W. F.; Zartun, D. L. J. Chem., Chem. Commun. 1984, 34-35. Mioskowski, C.; Manna, S.; Falck, J. R. Tetrahedron Lett. 1984, 25, 519-522. Venturello, P. J. Chem. Soc., Chem. Commun. 1992, 1032-1033. Canepa, C.; Prandi, C.; Sacchi, L.; Venturello, P. J. Chem. Soc., Perkin Trans. 1, 1993, 1875-1878. Deagostino, A.; Prandi, C.; Venturello, P. Tetrahedron 1996, 52, 1433-1442, and references therein.
14. Bailey, W. F.; Zartun, D. L. J. Chem., Chem. Commun. 1984, 34-35. Mioskowski, C.; Manna, S.; Falck, J. R. Tetrahedron Lett. 1984, 25, 519-522. Venturello, P. J. Chem. Soc., Chem. Commun. 1992, 1032-1033. Canepa, C.; Prandi, C.; Sacchi, L.; Venturello, P. J. Chem. Soc., Perkin Trans. 1, 1993, 1875-1878. Deagostino, A.; Prandi, C.; Venturello, P. Tetrahedron 1996, 52, 1433-1442, and references therein.
15. Bailey, W. F.; Zartun, D. L. J. Chem., Chem. Commun. 1984, 34-35. Mioskowski, C.; Manna, S.; Falck, J. R. Tetrahedron Lett. 1984, 25, 519-522. Venturello, P. J. Chem. Soc., Chem. Commun. 1992, 1032-1033. Canepa, C.; Prandi, C.; Sacchi, L.; Venturello, P. J. Chem. Soc., Perkin Trans. 1, 1993, 1875-1878. Deagostino, A.; Prandi, C.; Venturello, P. Tetrahedron 1996, 52, 1433-1442, and references therein.
16. Bailey, W. F.; Zartun, D. L. J. Chem., Chem. Commun. 1984, 34-35. Mioskowski, C.; Manna, S.; Falck, J. R. Tetrahedron Lett. 1984, 25, 519-522. Venturello, P. J. Chem. Soc., Chem. Commun. 1992, 1032-1033. Canepa, C.; Prandi, C.; Sacchi, L.; Venturello, P. J. Chem. Soc., Perkin Trans. 1, 1993, 1875-1878. Deagostino, A.; Prandi, C.; Venturello, P. Tetrahedron 1996, 52, 1433-1442, and references therein.
17. Bailey, W. F.; Zartun, D. L. J. Chem., Chem. Commun. 1984, 34-35. Mioskowski, C.; Manna, S.; Falck, J. R. Tetrahedron Lett. 1984, 25, 519-522. Venturello, P. J. Chem. Soc., Chem. Commun. 1992, 1032-1033. Canepa, C.; Prandi, C.; Sacchi, L.; Venturello, P. J. Chem. Soc., Perkin Trans. 1, 1993, 1875-1878. Deagostino, A.; Prandi, C.; Venturello, P. Tetrahedron 1996, 52, 1433-1442, and references therein.
18. t-BuLi has been shown to exist as a monomer in THF: Bauer, W,; Winchester, W. R.; Schleyer, P. v. R. Organometallics 1987, 6, 2371-2379. Here MeLi is considered just as a simple model for t-BuLi: as a consequence aggregation problems (see ref. 6) are plainly neglected in this study.
19. About the oligomerization of alkyllithiums, see: Kaufmann, E.; Gose, J.; Schleyer, P. v. R. Organometallics 1989, 8, 2577-2584; Kaufmann, E.; Raghavachari, K.; Reed, A. E.; Schleyer, P. v. R. Organometallics 1988, 7, 1597-1607 and references therein.
20. About the oligomerization of alkyllithiums, see: Kaufmann, E.; Gose, J.; Schleyer, P. v. R. Organometallics 1989, 8, 2577-2584; Kaufmann, E.; Raghavachari, K.; Reed, A. E.; Schleyer, P. v. R. Organometallics 1988, 7, 1597-1607 and references therein.
21. - distance of ca. 3.02 Å, instead of the more usual 2.88-2.89 Å. Ghigo, G.; Tonachini, G.; Venturello, P. Tetrahedron 1996, 52, 7053-7062.
22. Ghigo, G.; Tonachini, G.; Fossey, J. (submitted for publication).
23. Schlegel, H. B. in Computational Theoretical Organic Chemistry, Csizsmadia, I. G.; Daudel, R. Eds. Reidel Publ. Co.: Dordretch 1981, 129. Schlegel, H. B. J. Chem. Phys. 1982, 77, 3676-3681. Schlegel, H. B.; Binkley, J. S.; Pople, J. A. J. Chem. Phys. 1984, 80, 1976-1981. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214-218.
24. Schlegel, H. B. in Computational Theoretical Organic Chemistry, Csizsmadia, I. G.; Daudel, R. Eds. Reidel Publ. Co.: Dordretch 1981, 129. Schlegel, H. B. J. Chem. Phys. 1982, 77, 3676-3681. Schlegel, H. B.; Binkley, J. S.; Pople, J. A. J. Chem. Phys. 1984, 80, 1976-1981. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214-218.
25. Schlegel, H. B. in Computational Theoretical Organic Chemistry, Csizsmadia, I. G.; Daudel, R. Eds. Reidel Publ. Co.: Dordretch 1981, 129. Schlegel, H. B. J. Chem. Phys. 1982, 77, 3676-3681. Schlegel, H. B.; Binkley, J. S.; Pople, J. A. J. Chem. Phys. 1984, 80, 1976-1981. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214-218.
26. Schlegel, H. B. in Computational Theoretical Organic Chemistry, Csizsmadia, I. G.; Daudel, R. Eds. Reidel Publ. Co.: Dordretch 1981, 129. Schlegel, H. B. J. Chem. Phys. 1982, 77, 3676-3681. Schlegel, H. B.; Binkley, J. S.; Pople, J. A. J. Chem. Phys. 1984, 80, 1976-1981. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214-218.
27. For K / C,O / Li / H, the basis consists of (13s,8p / 7s,5p,1d / 7s,1p / 4s) gaussians, respectively, which are grouped as: 43321 (s) and 431 (p) for K; 421 (s), 311 (p), and 1 (d, the polarization set) for C and O; 421 (s) and 1 (p) for Li; 31 for H. This provides a [53/331/31/2] basis set.
28. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618. Binkley, J. S.; Pople, J. A. Int. J. Quantum Chem. 1975, 9, 229-236. Pople, J. A.; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. Symp. 1976, 10, 1-19. Krishnan, R.; Pople, J. A. Int. J. Quantum Chem. 1978, 14, 91-100.
29. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618. Binkley, J. S.; Pople, J. A. Int. J. Quantum Chem. 1975, 9, 229-236. Pople, J. A.; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. Symp. 1976, 10, 1-19. Krishnan, R.; Pople, J. A. Int. J. Quantum Chem. 1978, 14, 91-100.
30. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618. Binkley, J. S.; Pople, J. A. Int. J. Quantum Chem. 1975, 9, 229-236. Pople, J. A.; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. Symp. 1976, 10, 1-19. Krishnan, R.; Pople, J. A. Int. J. Quantum Chem. 1978, 14, 91-100.
31. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618. Binkley, J. S.; Pople, J. A. Int. J. Quantum Chem. 1975, 9, 229-236. Pople, J. A.; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. Symp. 1976, 10, 1-19. Krishnan, R.; Pople, J. A. Int. J. Quantum Chem. 1978, 14, 91-100.
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35. 15 The ε value was set to 7.6 (THF). This rough estimate did not bring about significant changes in the energy differences introduction of solvent effects, while keeping the optimized gas-phase geometries fixed, does not change significantly the preference for the addition pathway.
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