Theoretical studies on cyclopropanation reaction with lithium and zinc carbenoids

Chemistry Letters

Volumn , Issue 9, 1998, Pages 927-928

  Hirai, Atsushi ^a   Nakamura, Masaharu ^a   Nakamura, Eiichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032339477     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.927     Document Type: Article

References (26)

1. P. Helquist, in "Comprehensive Organic Synthesis", ed. by B. M. Trost, I. Fleming, C. H. Heathcock, S. V. Ley, R. Noyori, L. A. Raquette, G. Pattenten, S. L. Schreiber, M. F. Semmelhack, and E. Winterfeld, Pergamon Press (1991), Vol. 4, Chap. 4.6, p. 951.
2. H. E. Simmons, T. L. Crairns, S. A. Vladuchik, and C. M. Hoiness, Org. React., 20, 1 (1973). A. Streitwieser, Jr., and C. H. Heathcock, in "Introduction to Organic Chemistry, third edition", Macmillan Publishing Company (1989), Chap. 11, p. 268.
3. H. E. Simmons, T. L. Crairns, S. A. Vladuchik, and C. M. Hoiness, Org. React., 20, 1 (1973). A. Streitwieser, Jr., and C. H. Heathcock, in "Introduction to Organic Chemistry, third edition", Macmillan Publishing Company (1989), Chap. 11, p. 268.
4. S. E. Denmark and S. P. O'Connor, J. Org. Chem., 6 2, 584 (1997). E. C. Friedrich, S. E. Lunetta, and E. J. Lewis, J. Org. Chem., 5 4, 2388 (1989). A. B. Charette and H. Juteau, J. Am. Chem. Soc., 116, 2651 (1994). A. B. Charette, S. Prescott, and C. Brochu, J. Org. Chem., 6 0, 1081 (1995).
5. S. E. Denmark and S. P. O'Connor, J. Org. Chem., 6 2, 584 (1997). E. C. Friedrich, S. E. Lunetta, and E. J. Lewis, J. Org. Chem., 5 4, 2388 (1989). A. B. Charette and H. Juteau, J. Am. Chem. Soc., 116, 2651 (1994). A. B. Charette, S. Prescott, and C. Brochu, J. Org. Chem., 6 0, 1081 (1995).
6. S. E. Denmark and S. P. O'Connor, J. Org. Chem., 6 2, 584 (1997). E. C. Friedrich, S. E. Lunetta, and E. J. Lewis, J. Org. Chem., 5 4, 2388 (1989). A. B. Charette and H. Juteau, J. Am. Chem. Soc., 116, 2651 (1994). A. B. Charette, S. Prescott, and C. Brochu, J. Org. Chem., 6 0, 1081 (1995).
7. S. E. Denmark and S. P. O'Connor, J. Org. Chem., 6 2, 584 (1997). E. C. Friedrich, S. E. Lunetta, and E. J. Lewis, J. Org. Chem., 5 4, 2388 (1989). A. B. Charette and H. Juteau, J. Am. Chem. Soc., 116, 2651 (1994). A. B. Charette, S. Prescott, and C. Brochu, J. Org. Chem., 6 0, 1081 (1995).
8. J. G. White, T.-S. Kim, and M. Nambu, J. Am. Chem. Soc., 119, 103 (1997). A. G. M. Barrett and K. Kasdorf, J. Am. Chem. Soc., 118, 11030 (1996).
9. J. G. White, T.-S. Kim, and M. Nambu, J. Am. Chem. Soc., 119, 103 (1997). A. G. M. Barrett and K. Kasdorf, J. Am. Chem. Soc., 118, 11030 (1996).
10. G. Wittig and F. Wingler, Chem. Ber., 97, 2146 (1964).
11. F. Bernardi, A. Bottini, and G. P. Miscione, J. Am. Chem. Soc., 119, 12300 (1997).
12. H. C. Stiasny and R. W. Hoffmann, Chem. Euro. J., 1, 619 (1995).
13. E. Nakamura, A. Hirai, and M. Nakamura, J. Am. Chem.Soc., 120, 5844 (1998).
14. S. E. Denmark and S. P. O'Connor, J. Org. Chem., 6 2, 3390 (1997).
15. K. Kubota and E. Nakamura Angew. Chem. Int. Ed., 36, 2491 (1997). M. Nakamura, M. Arai, and E. Nakamura, J. Am. Chem. Soc., 117, 1179 (1995). M. Nakamura, E. Nakamura, N. Koga, and K. Morokuma, J. Chem. Soc. FaradayTrans., 90, 1789 (1994). E. Nakamura, S. Mori, M. Nakamura, and K. Morokuma, J. Am. Chem. Soc., 119, 4887 (1997).
16. K. Kubota and E. Nakamura Angew. Chem. Int. Ed., 36, 2491 (1997). M. Nakamura, M. Arai, and E. Nakamura, J. Am. Chem. Soc., 117, 1179 (1995). M. Nakamura, E. Nakamura, N. Koga, and K. Morokuma, J. Chem. Soc. FaradayTrans., 90, 1789 (1994). E. Nakamura, S. Mori, M. Nakamura, and K. Morokuma, J. Am. Chem. Soc., 119, 4887 (1997).
17. K. Kubota and E. Nakamura Angew. Chem. Int. Ed., 36, 2491 (1997). M. Nakamura, M. Arai, and E. Nakamura, J. Am. Chem. Soc., 117, 1179 (1995). M. Nakamura, E. Nakamura, N. Koga, and K. Morokuma, J. Chem. Soc. FaradayTrans., 90, 1789 (1994). E. Nakamura, S. Mori, M. Nakamura, and K. Morokuma, J. Am. Chem. Soc., 119, 4887 (1997).
18. K. Kubota and E. Nakamura Angew. Chem. Int. Ed., 36, 2491 (1997). M. Nakamura, M. Arai, and E. Nakamura, J. Am. Chem. Soc., 117, 1179 (1995). M. Nakamura, E. Nakamura, N. Koga, and K. Morokuma, J. Chem. Soc. FaradayTrans., 90, 1789 (1994). E. Nakamura, S. Mori, M. Nakamura, and K. Morokuma, J. Am. Chem. Soc., 119, 4887 (1997).
19. We used the density functional B3LYP method implemented in Gaussian 94 program (GAUSSIAN 94, revision E.I, M. J. Frisch, et al., GAUSSIAN Inc.; Pittsburgh, PA, USA, 1995). Ahlrichs's SVP (A. Schäfer, H. Horn, and R. Ahlrichs, J. Chem. Phys., 97, 2571 (1992).) basis set was used for zinc atom and 6-31G* basis sel for other atoms (denoted here as B3LYP/631A).
20. We used the density functional B3LYP method implemented in Gaussian 94 program (GAUSSIAN 94, revision E.I, M. J. Frisch, et al., GAUSSIAN Inc.; Pittsburgh, PA, USA, 1995). Ahlrichs's SVP (A. Schäfer, H. Horn, and R. Ahlrichs, J. Chem. Phys., 97, 2571 (1992).) basis set was used for zinc atom and 6-31G* basis sel for other atoms (denoted here as B3LYP/631A).
21. basis set was used for zinc atom and 6-31G* basis sel for other atoms (denoted here as B3LYP/631A).
22. 3; 1.008 in TSmZn (scale factor of 0.9804; M. W. Wong, Chem. Phys. Lett., 255, 391 (1996); E. P. Wigner, Z. Phys. Chem., B19, 203 (1932). J. Bigeleisen, J. Chem. Phys., 17, 675 (1949).). The trend in KIEs for TSmZn differs significantly from that of TScZn, and will be a measure to experimentally differenciate the two pathways.
23. 3; 1.008 in TSmZn (scale factor of 0.9804; M. W. Wong, Chem. Phys. Lett., 255, 391 (1996); E. P. Wigner, Z. Phys. Chem., B19, 203 (1932). J. Bigeleisen, J. Chem. Phys., 17, 675 (1949).). The trend in KIEs for TSmZn differs significantly from that of TScZn, and will be a measure to experimentally differenciate the two pathways.
24. 3; 1.008 in TSmZn (scale factor of 0.9804; M. W. Wong, Chem. Phys. Lett., 255, 391 (1996); E. P. Wigner, Z. Phys. Chem., B19, 203 (1932). J. Bigeleisen, J. Chem. Phys., 17, 675 (1949).). The trend in KIEs for TSmZn differs significantly from that of TScZn, and will be a measure to experimentally differenciate the two pathways.
25. 2l is 13.1 kcal/mol (B3LYP/631A).
26. 1-Cl bond without ethylene, we obtained a zinc carbene complex structure, which was however a TS of chlorine atom exchange reaction (the vector of negative frequency shown by arrows). matrix presented