Reaction of β-fluorovinamidinium salt with grignard reagents. Facile and efficient route to (Z)-α-fluoro-α,β-unsaturated aldehydes

Tetrahedron Letters

Volumn 39, Issue 38, 1998, Pages 6943-6946

  Yamanaka, Hiroki ^a   Odani, Yasumasa ^a   Ishihara, Takashi ^a   Gupton, John T ^b  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

^b UNIVERSITY OF NORTH CAROLINA AT ASHEVILLE   (United States)

Author keywords

Aldehydes; Fluorine and compounds; Grignard reactions reagents; Vinamidmium salts

Indexed keywords

ALDEHYDE; AMIDINE; BETA FLUOROVINAMIDINIUM SALT; GRIGNARD REAGENT; HYDRAZINE DERIVATIVE; HYDROXYLAMINE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; BINDING KINETICS; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; ORGANIC CHEMISTRY; REACTION ANALYSIS; STRUCTURE ANALYSIS; TEMPERATURE MEASUREMENT;

EID: 0032541683     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01459-2     Document Type: Article

References (25)

1. [1] Lloyd D, McNab H. Angew. Chem. Int. Ed. Engl. 1976;15:459-468 and references therein.
2. [2] Jutz C, Lobering HG, Trinkl KH. Synthesis 1977:326-327.
3. [3] Adams F, Gompper R, Kujath E. Angew. Chem. Int. Ed. Engl. 1989;28:1060-1065.
4. [4] Gupton JT, Gall JE, Riesinger SW, Smith SQ, Bevirt KM, Sikorski JA, Dahl ML, Arnold Z. J. Heterocyclic Chem. 1991;28:1281-1285.
5. [5] Petrich SA, Hickes FA, Wilkinson DR, Tarrant JG, Bruno SM, Vargas M, Hosein KN, Gupton JT, Sikorski JA. Tetrahedron 1995:51;1575-1584.
6. [6] Nair V, Cooper CS. Tetrahedron Lett. 1980;21:3155-3158.
7. [7] Nair V, Cooper CS. J. Org. Chem. 1981;46:4759-4765.
8. [8] Gupton JT, Krolikowski DA, Yu RH, Riesinger SW, Sikorski JA. J. Org. Chem. 1990:55;4735-4740.
9. [9] Gupton JT, Riesinger SW, Shah AS, Gall JE, Bevirt KM. J. Org. Chem. 1991;56:976-980.
10. [10] Ehmann A, Gompper R, Hartmann H, Muller TJJ, Polborn K, Schutz R. Angew. Chem. Int. Ed. Engl. 1994;33: 572-575.
11. [11] Payrastre C, Obaya N, Madaule Y, Wolf JG. Tetrahedron Lett. 1994;35:3059-3062.
12. [12] Cotton FA, Daniels LM, Haefner SC, Murillo CA. J. Chem. Soc., Chem. Commun. 1996;2507-2508.
13. [13] Reichardt C, Halbritter K. Justus Liebigs Ann. Chem. 1970;737:99-107.
14. [14] Reichardt C, Halbritter K. Justus Liebigs Ann. Chem. 1975:470-483.
15. [15] Saloutin VI, Skryabina ZE, Burgart YV, Chupakhin ON, Font-Altaba M, Solans X, Font-Bardia M. J. Fluorine Chem. 1994;69:25-29.
16. [16] Yamanaka H, Yamashita S, Ishihara T. Tetrahedron Lett. 1992;33:357-360.
17. [17] Yamanaka H, Takekawa T, Morita K, Ishihara T. Tetrahedron Lett. 1996;37:1829-1832.
18. [18] Kase K, Katayama M, Ishihara T, Yamanaka H, Gupton JT. Chem. Lett. 1997:893-894.
19. [19] Shi X, Ishihara T, Yamanaka H, Gupton JT. Tetrahedron Lett. 1995;36:1527-1530.
20. [20] Kase K, Katayama M, Ishihara T, Yamanaka H, Gupton JT. J. Fluorine Chem. in press.
21. [21] Yamanaka H, Yamashita S, Ishihara T. Synlett 1993:353-353.
22. [22] Yamanaka H, Hisaki K, Kase K, Ishihara T, Gupton JT. Tetrahedron Lett. 1998;39:4355-4358
23. [23] Funabiki K, Fukushima Y, Inagaki T, Murata E, Matsui M, Shibata K. Tetrahedron Lett. 1998:39;1913-1916.
24. 7FO 150.0481, Found 150.0475.
25. [25] Jackman LM, Sternhell S. Nuclear magnetic resonance spectroscopy in organic chemistry. 2nd ed.,Sidney: Pergamon Press, 1969:316.