A new method for the preparation of fluoro-λ6-sulfanenitriles: Reaction of sulfimides with Selectfluor™

Tetrahedron Letters

Volumn 44, Issue 33, 2003, Pages 6203-6205

  Fujii, Takayoshi ^a   Asai, Shinsuke ^a   Okada, Tomoyuki ^a   Hao, Wei ^a   Morita, Hiroyuki ^a   Yoshimura, Toshiaki ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Fluorination; Fluoro 6 sulfanenitriles; Heterocycles; Selectfluor ; Sulfimides; X ray crystallographic analysis

Indexed keywords

IMIDE; NITRILE;

ARTICLE; CHEMICAL REACTION; MOLECULAR SIZE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0041846796     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01547-8     Document Type: Article

References (28)

1. Haase J., Oberhammer H., Zeil W., Glemser O., Mews R. Z. Naturforsch. 25a:1970;153-156.
2. Oberhammer H., Kumar R.C., Knerr G.D., Shreeve J.M. Inorg. Chem. 20:1981;3871-3874.
3. Burtzoff M.D., Peter L., Lepse P.A., Zhang D.Y. J. Mol. Struct. (THEOCHEM). 619:2002;229-239.
4. Mews R., Glemser O. Inorg. Nucl. Chem. Lett. 6:1970;35-38.
5. Kumar R.C., Shreeve J.M. J. Am. Chem. Soc. 103:1981;1951-1952.
6. Oae S., Furukawa N. Sulfilimines and Related Derivatives. 1983;American Chemical Society, Washington, DC.
7. Gilchrist T.L., Moody C.J. Chem. Rev. 77:1977;409-435. and references cited therein.
8. Yoshimura T., Furukawa N., Akasaka T., Oae S. Tetrahedron. 33:1977;1061-1067.
9. Yoshimura T. Rev. Heteroat. Chem. 22:2000;101-120. and references cited therein.
10. Yoshimura T., Ohkubo M., Fujii T., Kita H., Wakai Y., Ono S., Morita H., Shimasaki C., Horn E. Bull. Chem. Soc. Jpn. 71:1998;1629-1637.
11. Yoshimura T., Takata E., Miyake T., Shimasaki C., Hasegawa K., Tsukurimichi E. Chem. Lett. 1992;2213-2216.
12. Yoshimura T., Hamada K., Imado M., Hamata K., Tomoda K., Fujii T., Morita H., Shimasaki C., Ono S., Tsukurimichi E., Furukawa N., Kimura T. J. Org. Chem. 62:1997;3802-3803.
13. Yoshimura T., Fujii T., Murotani S., Miyoshi S., Fujimori T., Ohkubo M., Ono S., Morita H. J. Organomet. Chem. 611:2000;272-279.
14. Fujii T., Fujimori T., Miyoshi S., Murotani S., Ohkubo M., Yoshimura T. Heteroat. Chem. 12:2001;263-268.
15. Fujii T., Itoh A., Hamata K., Yoshimura T. Tetrahedron Lett. 42:2001;5041-5043.
16. Fujii T., Suzuki T., Sato T., Horn E., Yoshimura T. Tetrahedron Lett. 42:2001;6151-6154.
17. Glemser O., Mews R., Roesky H.W. J. Chem. Soc., Chem. Commun. 1969;914.
18. Glemser O., Mews R. Angew. Chem., Int. Ed. Engl. 19:1980;883-899. and references cited therein.
19. For Selectfluor™, see: (a) Lal, G. S.; Pez, G. P.; Syvret, R. G. Chem. Rev. 1996, 96, 1737-1755; (b) Singh, R. P.; Shreeve, J. M. Chem. Commun. 2001, 1196-1197; (c) Majumder, U.; Armantrout, J. R.; Williams, R. V.; Shreeve, J. M. J. Org. Chem. 2002, 67, 8435-8439.
20. For Selectfluor™, see: (a) Lal, G. S.; Pez, G. P.; Syvret, R. G. Chem. Rev. 1996, 96, 1737-1755; (b) Singh, R. P.; Shreeve, J. M. Chem. Commun. 2001, 1196-1197; (c) Majumder, U.; Armantrout, J. R.; Williams, R. V.; Shreeve, J. M. J. Org. Chem. 2002, 67, 8435-8439.
21. For Selectfluor™, see: (a) Lal, G. S.; Pez, G. P.; Syvret, R. G. Chem. Rev. 1996, 96, 1737-1755; (b) Singh, R. P.; Shreeve, J. M. Chem. Commun. 2001, 1196-1197; (c) Majumder, U.; Armantrout, J. R.; Williams, R. V.; Shreeve, J. M. J. Org. Chem. 2002, 67, 8435-8439.
22. 6-sulfanenitriles. See: Dong T., Fujii T., Murotani S., Dai H., Ono S., Morita H., Shimasaki C., Yoshimura T. Bull Chem. Soc. Jpn. 74:2001;945-954.
23. Gaussian 98, Revision A.9, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1998.
24. Morita H., Kawaguchi H., Yoshimura T., Tsukurimichi E., Shimasaki C., Horn E. Chem. Eur. J. 6:2000;3976-3983.
25. 3CN at 50°C, which gave the intractable complex mixture.
26. 2: C, 51.23; H, 2.87; N, 4.98. Found: C, 51.29; H, 2.93; N, 5.02.
27. int=0.007). The final R values was 0.039. Crystallographic data for the structural analysis has been deposited with the Cambridge Crystallographic Data Centre, CCDC No. 211241 for compound 5.
28. Horn E., Dong T., Fujii T., Yoshimura T., Shimasaki C. Z. Kristallogr. NCS. 215:2000;356-357.