The preparation of (EtO)2P(O)CFHZnBr and (EtO)2P(O)CFHCu and their utility in the preparation of functionalized α-fluorophosphonates

Tetrahedron Letters

Volumn 40, Issue 14, 1999, Pages 2681-2684

  Zhang, Xin ^a   Weiming, Qiu ^a   Burton, Donald J ^a  

^a The University of Iowa ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; FLUOROPHOSPHONATE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; ZINC BROMIDE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; FLUORINATION; REACTION ANALYSIS; STEREOISOMERISM; SYNTHESIS; THERMOSTABILITY;

EID: 0033515719     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00305-6     Document Type: Article

References (21)

1. a) Engel R, Chem. Rev. 1977:77:349-367;
2. b) Blackburn GM, Perree TD, Rashid A, Bisbal C, Lebleu B, Chem. Scr. 1986:26:21-24;
3. c) Adams PR, Harrison R, Inch TD, Biochem. J. 1974:141:729-732;
4. d) Cheng P-J, Hickey R, Engel R, Tropp BE, Biochem. Biophys. Acta 1974:341:85-92.
5. a) O'Hagan D, Rzepa HS, J. Chem. Soc., Chem. Commun. 1997:645-652;
6. b) Thatcher GRJ, Campbell AS, J. Org. Chem. 1993:58:2272-2281;
7. c) Nieschalk J, Batsanov AS, O'Hagan D, Howard JAK, Tetrahedron 1996:52:165-176.
8. a) Benayoud F, deMendonca DJ, Digits CA, Moniz GA, Sanders TC, Hammond GB, J. Org. Chem.1996:61:5159-5164 ;
9. b) Sanders TC, Hammond GB. J. Org. Chem. 1993:58:5598-5599;
10. c) Benayoud F, Chen L, Moniz GA, Zopato AJ, Hammond, GB, Tetrahedron 1998:54:15541-15554.
11. Chen W, Flavin MT, Filler R, Xu Z-Q, Tetrahedron Lett. 1996:37:8975-8978.
12. a) Blackburn GM, Kent DE, J. Chem. Soc. Perkin, Trans. I 1986:913-917;
13. b) Blackburn GM, Parratt MJ, J. Chem. Soc., Perkin Trans. I 1986:1417-1430;
14. c) Blackburn GM, Rashid A, J. Chem. Soc., Chem. Commun. 1988:317-319.
15. a) Waschbüsch R, Carran J, Marinetti A, Savignac P, Synthesis 1997:7:727-743;
16. b) Patois C, Savignac P, J. Chem. Soc. Chem. Commun. 1993:1711-1712;
17. c) Waschbüsch R, Carran J, Savignac P, J. Chem. Soc., Perkin Trans. I 1997:1135-1139;
18. d) Patois C, Savignac P, Synth. Commun. 1994:24:1317-1322;
19. e) Iorga B, Eymery F, Savignac P, Tetrahedron Lett. 1998:39:4477-4480.
20. Zhang X, Qiu W, Burton DJ, J. Fluorine Chem. 1998:89:39-49.
21. 19F NMR, δ = -266 ± 0.5 ppm (t, J = 52 Hz) in solvents such as THF, THF/DMF, THF/DMAC, DMF and triglyme.