Synthesis of PO(OR)2- and PR3+-disubstituted pyridines via N- (trifluoromethylsulfonyl)pyridinium triflates

Synthesis

Volumn , Issue 2, 1998, Pages 195-200

  Haase, Mirko ^a   Goerls, Helmar ^a   Anders, Ernst ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

C2 and C4 disubstituted pyridines; N (trifluoromethylsulfonyl)pyridinium triflates; Phosphites; Phosphonium triflates; Regioselective nucleophilic substitution

Indexed keywords

2,4 BIS(DIALKOXYPHOSPHORYL)PYRIDINE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; [2 (DIALKOXYPHOSPHORYL) 4 PYRIDYL]TRIPHENYLPHOSPHONIUM DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL REACTION; PURIFICATION; REACTION ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 0031937283     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-2012     Document Type: Article

References (24)

1. Russel, A. A.; Meline, R. L.; Duestler, E. N.; Paine, R. T. Inorg. Chim. Acta 1995, 231, 1.
2. For reviews on Pyridylphosphines: Newcome, G. R. Chem. Rev. 1993, 93, 2067.
3. Spiegel, G. U.; Stelzer, O. Chem. Ber. 1990, 123, 989.
4. Beugelmans, R.; Chbani, M. Bull. Soc. Chim. Fr. 1995, 132, 290.
5. Desos, P.; Lestage, P.; Cordi, A. A. J. Med. Chem. 1996, 1, 197.
6. Schull, T. L.; Fettinger, J. C.; Knight, D. A. J. Chem. Soc., Chem. Commun. 1995, 1487.
7. Salomon, C. J.; Breuer, E. Tetrahedron Lett. 1995, 36, 6759.
8. Akiba, K.; Matsuoka, H.; Wada, M. Tetrahedron Lett. 1981, 22, 4093.
9. Redmore, D. J. Org. Chem. 1970, 35, 4114.
10. Katritzky, A. R.; Keay, J. G.; Sammes, M. P. J. Chem. Soc., Perkin Trans 1 1981, 668.
11. Redmore, D. J. Org. Chem. 1976, 41, 2148.
12. Moshchitskii, S. D.; Sologub, L. S.; Pavlenko, A. F.; Kukhar, V. P. Zh. Obshch. Khim. 1977, 47, 1263.
13. Anders, E.; Markus, F. Chem. Ber. 1989, 122, 113.
14. Anders, E.; Markus, F. Chem. Ber. 1989, 122, 119.
15. The results of a detailed mechanistic and structural study based on ab initio and semiempirical calculations will be published separately.
16. Akiba, K.; Negishi, Y.; Inamoto, N. Synthesis 1979, 55.
17. After isolation, the compounds 7 and 8 are stable at ca. 5-10°C for several days.
18. 3 → 7 + 8 becomes irreversible.
19. 2 gives slightly better results.
20. 3H. Neither the bromide nor the triflate reacts with phosphites.
21. MOLEN, An Interactive Structure Solution Procedure, Enraf-Nonius, Delft, The Netherlands, 1990.
22. Sheldrick G.M. Acta Crystallogr., Sect. A 1990, 46, 467.
23. Sheldrick G.M., SHELXL-93, University of Göttingen, Germany, 1993.
24. Further details of the crystal structure investigations are available on request from the Fachinformationszentrum Karlsruhe, Gesellschaft für wissenschaftlich-technische Information mbH, D-76344 Eggenstein-Leopoldshafen (Germany), on quoting the depository number CSD-406873, the names of the authors, and the journal citation.