Constitution of Grignard reagent RMgCI in tetrahydrofuran

Organic Letters

Volumn 3, Issue 12, 2001, Pages 1793-1795

  Sakamoto, Shigeru ^a   Imamoto, Tsuneo ^a   Yamaguchi, Kentaro ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000953764     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010048x     Document Type: Article

References (26)

1. (a) Wakefield, B. J. Organomagnesium Methods in Organic Synthesis; Academic Press: London, 1995.
2. (b) Silverman, G. S.; Rakita, P. E. Handbook of Grignard Reagents: Marcel Dekker: New York, 1996.
3. Schlenk, W.; Schlenk, W., Jr. Ber. Dtsch. Chem. Ges. 1929, 62, 920-924.
4. (a) Ashby, E. C.; Becker, W. E. J. Am. Chem. Soc. 1963, 85, 118-119.
5. (b) Ashby, E. C.; Smith, M. B. J. Am. Chem. Soc. 1964, 86, 4363-4370.
6. Tony, J.; Stucky, G. D. J. Organomet. Chem. 1971, 28, 5-20.
7. Sobota, P.; Duda, B. J. Organomet. Chem. 1987, 332, 239-245.
8. Sakamoto, S.; Fujita, M.; Kim, K.; Yamaguchi, K. Tetrahedron 2000, 56, 955-964.
9. (a) Yamashita, M.; Fenn, J. B. J. Phys. Chem. 1984, 88, 4451-4459.
10. (b) Fenn, J. B.; Mann, M.; Meng, K.; Wong, S. F.; Whitehouse, C. M. Science 1989, 246, 64-71.
11. (c) Kebarle, P.; Tang, L. Anal. Chem. 1993, 65, 972A-986A.
12. (c) Bruins, A. P. J. Chromatogr. A 1998, 794, 345-357.
13. (a) Ikeda, A.; Ayabe, M.; Shinkai, S.; Sakamoto, S.; Yamaguchi, K. Org. Lett. 2000, 2, 3707-3710.
14. (b) Yamanoi, Y.; Sakamoto, Y.; Kusukawa, T.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. J. Am. Chem. Soc. 2001, 123, 980-981.
15. (c) Zhong, Z.; Ikeda, A.; Ayabe, M.; Shinkai, S. Sakamoto, S.; Yamaguchi, K. J. Org. Chem. 2001, 66, 1002-1008.
16. Single crystals were obtained from MeMgCl, tBuMgCl, PhMgCl, and benzylMgCl in THF by addition of dry hexane (10% vol) to a 4-5 M solution under argon in a Schlenk tube. These single crystals were enclosed in a capillary tube under nitrogen in a glovebox. A Bruker SMART CCD diffractometer or Rigaku RAXISIIC imaging plate diffractometer was used.
17. The Mg-Mg distances are 3.169(3) and 3.192(6) Å in the cases of tBuMgCl and PhMgCl, respectively. These distances are significantly shorter than the sum of two magnesium radii (3.46 Å), even though these Mg atoms probably repel each other owing to their positive charges.
18. w = 0.124.
19. w = 0.145.
20. w = 0.097.
21. w = 0.146.
22. w = 0.074.
23. 6 obtained from EtMgCl, which was previously analyzed by Tony and Stucky.
24. w; = 0.110.
25. 3).
26. CSI-MS spectrum measurement was performed with a four-sector (BE/BE) tandem mass spectrometer (JMS-700T, JEOL) equipped with the CSI source. Typical measurement conditions are as follows: (CSI-MS) acceleration voltage, 5.0 kV; needle voltage, 2.8 kV; needle current, 300-700 nA; orifice voltage, 50 V; resolution (10% valley definition), 1000; sample flow, 33 μL/min; solvent, dry THF; concentration, 10 mmol/L; spray temperature, -20°C; ion source temperature, 10°C. (MS/MS) acceleration voltage, 5.0 kV; collision gas, Xe; collision cell voltage, 0 V.