Grignard reaction with chlorosilanes in THF: A kinetic study

Journal of Organic Chemistry

Volumn 69, Issue 15, 2004, Pages 5071-5076

  Tuulmets, Ants ^a   Nguyen, Binh T ^b   Panov, Dmitri ^a  

^a UNIVERSITY OF TARTU   (Estonia)

^b DOW CORNING CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHARGE TRANSFER; HYDROCARBONS; ORGANOMETALLICS; SILICON COMPOUNDS; STEREOCHEMISTRY;

CHLOROSILANES; GRIGNARD REACTIONS;

REACTION KINETICS;

CHLOROSILANE DERIVATIVE; HYDROCARBON; MAGNESIUM CHLORIDE; SILANE DERIVATIVE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; CONCENTRATION (PARAMETERS); EQUILIBRIUM CONSTANT; GRIGNARD REACTION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 3543035793     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0498361     Document Type: Article

References (34)

1. Arkles B. In Handbook of Grignard Reagents; Silverman, G. S., Rakita P. E., Eds.; Marcel Dekker: New York, 1996; Chapter 32.
2. (a) Reid, A. F.; Wilkins, C. J. J. Chem. Soc. 1955, 4029-4034. Corriu, R. J. P.; Henner, B. J. Organomet. Chem 1975, 102, 407-416.
3. (a) Reid, A. F.; Wilkins, C. J. J. Chem. Soc. 1955, 4029-4034. Corriu, R. J. P.; Henner, B. J. Organomet. Chem 1975, 102, 407-416.
4. (b) Tuulmets, A.; Hõrak, M.; Kõopere, T.; Ruotsi, J. Org. React. (USSR) 1982, 19, 102-119.
5. (c) Sassian, M.; Panov, D.; Tuulmets, A. Appl. Organomet. Chem. 2002, 16, 525-529.
6. (d) Tuulmets, A.; Panov, D.; Sassian, M. Tetrahedron Lett. 2003, 44, 3943-3945.
7. (e) Tuulmets, A.; Nguyen, B. T.; Panov, D.; Sassian, M.; Järv, J. J. Org. Chem. 2003, 68, 9933-9937.
8. (a) Lindsell, W. E. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon Press: Elmford, NY, 1982; Vol. 1, Chapter 4.
9. (b) Cannon, K. C.; Krow, G. R. In Handbook of Grignard Reagents; Silverman, G. S., Rakita. P. E., Eds.; Marcel Dekker: New York, 1996; Chapter 13.
10. (c) Holm, T.; Crossland I. In Grignard Reagents: New Developments; Richey, H. G., Jr., Ed.; J. Wiley: New York, 2000; Chapter 1.
11. Koppel, J.; Margna, L.; Tuulmets, A. Reakts. Sposobn. Org. Soedin. 1968, 5, 1041-1052.
12. Blomberg C. In Handbook of Grignard Reagents; Silverman, G. S., Rakita, P. E., Eds.; Marcel Dekker: New York, 1996; Chapter 11.
13. (a) Koppel, J.; Tuulmets, A. Reakts. Sposobn. Org. Soedin. 1970, 7, 911-918.
14. (b) Koppel, J.; Loit, J.; Luuk, M.; Tuulmets, A. Reakts. Sposobn. Org. Soedin. 1971, 8, 1155-1164.
15. (c) Koppel, J.; Tuulmets, A. Reakts. Sposobn. Org. Soedin. 1972, 9, 399-411.
16. (d) Viirlaid, S.; Kurikoff, S.; Tuulmets, A. Reakts. Sposobn. Org. Soedin. (USSR) 1974, 11, 73-80.
17. (e) Tuulmets, A.; Pällin, V.; Tammiku-Taul, J.; Burk, P.; Raie, K. J. Phys. Org. Chem. 2002, 15, 701-705.
18. Walker, F. W.; Ashby, E. C. J. Am. Chem. Soc. 1960, 91, 3845-3850.
19. Ashby, E. C.; Laemmle, J.; Neumann, H. M. Acc. Chem. Res. 1974, 7, 272-281.
20. (a) Schröder, F.; Spandau, H. Naturwissenschaften 1866, 53, 360-362.
21. (b) Perucaud, M.; Ducom, J.; Vallino, M. C. R. Acad. Sci. 1887, 264, 571-573.
22. Sarma, R.; Ramirez, F.; McKeever, B.; Chaw, Y. F.; Marecek, J. F.; Nierman, D.; McCaffrey, T. M. J. Am. Chem. Soc. 1977, 99, 5289-5295.
23. (a) Tammiku-Taul, J.; Burk, P.; Tuulmets, A. J. Phys. Chem. A 2004, 108, 133-139.
24. 2Mg·2THF -27.8.
25. Calculations were performed for chlorides and bromides.11a The cis-form is a deformed octahedron where two THF ligands are equatorial and the other two are axial. The trans-form is also an octahedron where equatorial and axial positions are indistinguishable.
26. Smith, M. B.; Becker, W. E. Tetrahedron 1887, 23, 4215-4219.
27. F is +2%, and if it is greater by 10%, the error is -3%.
28. 2.
29. Holm, T. Acta Chem. Scand. 1966, 20, 2821-2828.
30. Koppel, J.; Vaiga, S.; Tuulmets, A. Reakts. Sposobn. Org. Soedin 1970, 7, 898-910.
31. (a) Charton, M. J. Am. Chem. Soc. 1975, 97, 1552-1556.
32. (b) Taft, R. W. In Steric Effects in Organic Chemistry; Newman, M. S., Ed.; J. Wiley: New York, 1956; Chapter 13.
33. Wakefield, B. J. Organomagnesium Methods in Organic Synthesis; Academic Press: New York, 1995.
34. Rudakov, E. C. Kinet. Katal. 1960, 1, 177-183.