Ab Initio Mechanisms for the Addition of CH3Li, HLi, and Their Dimers to Formaldehyde

Journal of the American Chemical Society

Volumn 107, Issue 19, 1985, Pages 5560-5562

  Kaufmann, Elmar ^a   von Ragué Schleyer, Paul ^a   Houk, K N ^b   Wu, Yun Dong ^b  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845379409     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00305a058     Document Type: Article

References (16)

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2. McGarrity, J. F.; Ogle, C. A.; Brich, Z.; Loosli, H.-R. J. Am. Chem. Soc. 1985, 107, 1810. Also see: McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1805. See: Bacn, D.; Hassig, R.; Gabriel, J. Helv. Chim. Acta 1983, 66, 308.
3. McGarrity, J. F.; Prodolliet, J.; Smyth, T. Org. Magn. Reson. 1981, 17, 59. McGarrity, J. F.; Prodolliet, J. J. Org. Chem. 1984, 49, 4465.
4. (a) Smith, S. G.; Charbonneau, L. F.; Novak, D. P.; Brown, T. L. J. Am. Chem. Soc. 1972, 94, 7059. In hydrocarbon solvents: (b) Charbonneau, L. F.; Smith, S. G. J. Org. Chem. 1976, 41, 808. Al-Aseer, M. A.; Smith, S. G., J. Org. Chem. 1984, 49, 2608. Al-Aseer, M, A.; Allison, B. D.; Smith, S. G. J. Org. Chem. 1985, 50, 2715. For criticisms of the interpretation of such kinetic results, see: References 1 (p 14), 2, and: (c) Brown, T. L. J. Organomet. Chem. 1966, 5, 191; Adv. Organomet. Chem. 1965, 3, 365.
5. 2 solvated by four acetone molecules is reported in: Amstutz, R. Dissertation, ETH Zurich, 1983. For other, related examples see: a review: Setzer, W.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353.
6. See Del Bene, J. E.; Frisch, M. J.; Raghavachari, K.; Pople, J. A.; Schleyer, P. V. R. J. Phys. Chem. 1983, 87, 73 and references cited. Kaufmann, E., unpublished calculations. Smith, S. F.; Chandrasekhar, J.; Jorgensen, W. L. J. Phys. Chem. 1982, 86, 3308.
7. Biirgi, H. B.; Dunitz, J. D.; Lehn. J. M.; Wipff, G. Tetrahedron 1974, 30, 1563. Dunitz, J. D., “X-ray Analysis and the Structure of Organic Molecules”; Cornell University Press: Ithaca, NY, 1979: p 366 ff. Menger, F. M. Tetrahedron 1983, 39, 1013.
8. Also see, inter alia: Williams, I. H.; Spangler, D.; Femec, D. A.; Maggiora, G. M.; Schowen, R. L. J. Am. Chem. Soc. 1983, 105, 31. Eisenstein, O.; Schlegel, H. B.; Kayser, M. M. J. Org. Chem. 1982, 47, 2886. Liotta, C. L.; Burgess, E. M.; Eberhardt, W. H. J. Am. Chem. Soc. 1984, 106, 4849. Menger, F. M. Tetrahedron 1983, 39, 1013.
9. See, e.g.; Ashby, E. C.; Goel, A. B.; Argyropoulos, J. N. Tetrahedron Lett. 1982, 23, 2273. Ashby, E. C.; Argyropoulos, J. N.; Meyer, G. R.; Goel, A. B. J. Am. Chem. Soc. 1982, 104, 6788. Liotta, D.; Saindane, M.; Waykole, L. J. Am. Chem. Soc. 1983, 105, 2922.
10. Li, M.-Y.; Filippo, J. S., Jr. Organometallics 1983, 2, 554.
11. Vitale, A. A.; Filippo, J. S., Jr. J. Am. Chem. Soc. 1982, 104, 7341.
12. E.g.: Watson, P. L. J. Am. Chem. Soc. 1983, 105, 6491.
13. Houk, K. N.; Rondan, N. G.; Schleyer, P. V. R.; Kaufmann E.; Clark, T. J. Am. Chem. Soc. 1985, 107, 2821.
14. 4: Bonaccorsi, R.; Cimiraglia, R.; Tomasi, J.; Miertuš, S. J. Mol. Struct. 1983, 94, 11. Bonaccorsi, R.; Palla, P.; Tomasi, J. J. Mol. Struct. 1982, 87, 181.
15. 2,4
16. Bachrach, S. M.; Streitwieser, A., Jr., manuscript in preparation.