On the synthesis and NMR analysis of tetrabutylammonium triphenyldifluorosilicate

Journal of Organic Chemistry

Volumn 65, Issue 11, 2000, Pages 3542-3543

  Handy, Christopher J ^a   Lam, Yiu Fai ^a   DeShong, Philip ^a  

^a Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SILICATE; TETRABUTYLAMMONIUM;

CHEMICAL ANALYSIS; CHEMICAL REACTION; NOTE; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS;

MAGNETIC RESONANCE SPECTROSCOPY; ORGANOSILICON COMPOUNDS; QUATERNARY AMMONIUM COMPOUNDS;

EID: 0034595838     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991771s     Document Type: Note

References (22)

1. Pilcher, A. S.; Ammon, H. L.; DeShong, P. J. Am. Chem. Soc. 1995, 117, 5166-5167.
2. Albanese, D.; Landini, D.; Penso, M. Tetrahedron Lett. 1995, 36, 8865-8866.
3. Shibata, K.; Miyazawa, K.; Goto, Y. J. Chem. Soc., Chem. Commun. 1997, 1309-1310.
4. Scheidt, K. A.; Chen, H.; Follows, B. C.; Chemler, S. R.; Coffey, D. S.; Roush, W. R. J. Org. Chem. 1998, 63, 6436-6437.
5. Mowery, M. E.; DeShong, P. J. Org. Chem. 1999, 64, 1684-1688.
6. Soli, E. D.; Manoso, A. S.; Patterson, M. C.; DeShong, P.; Favor, D. A.; Hirschmann, R.; Smith, A. B., III. J. Org. Chem. 1999, 64, 3171-3177.
7. Soli, E. D.; DeShong, P. J. Org. Chem. 1999, 64, 9724-9726.
8. Mowery, M. E.; DeShong, P. Org. Lett. 1999, 1, 2137-2140.
9. Albanese, D.; Landini, D.; Penso, M.; Petricci, S. Synlett 1999, 199-200.
10. Hojo, M.; Murakami, C.; Fujii, A.; Hosomi, A. Tetrahedron Lett. 1999, 40, 911-914.
11. Gurvich, V.; Kim, H.-Y.; Hodge, R. P.; Harris, C. M.; Harris, T. M. Nucleosides Nucleotides 1999, 18, 2327-2333.
12. Denmark, S. E.; Choi, J. Y. J. Am. Chem. Soc. 1999, 121, 5821-5822.
13. Denmark, S. E.; Wu, Z. Org. Lett. 1999, 1, 1495-1498.
14. Denmark, S. E.; Wehrli, D. Org. Lett. 2000, 2, 565-568.
15. Chuit, C.; Corriu, R. J. P.; Reye, C. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley-VCH: New York, 1999; pp 81-146.
16. Kira, M.; Zhang, L. C. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley-VCH: New York, 1999; pp 147-169.
17. Pilcher, A. S.; DeShong, P. J. Org. Chem. 1996, 61, 6901-6905.
18. Brescia, M.-R.; DeShong, P. J. Org. Chem. 1998, 63, 3156-3157.
19. Mowery, M. E.; DeShong, P. J. Org. Chem. 1999, 64, 3266-3270.
20. Sharma, R. K.; Fry, J. L. J. Org. Chem. 1983, 48, 2112-2114.
21. Marat, R. K.; Janzen, A. F. J. Chem. Soc., Chem. Commun. 1977, 671-672.
22. 19F spectroscopy to check the purity of the 1.0 M solution of TBAF in THF prior to its use in the synthesis, as varying amounts of bifluoride and other contaminants are often present in commercially available solutions purchased from Acros and Aldrich. Alternatively, the Denmark group recommends preparation of 1.0 M TBAF in THF from crystalline TBAF purchased from Fluka. These prepared solutions contain <1% bifluoride and are stable indefinitely.