The effect of the reaction conditions on the course of the reactions of hindered phenols with N-F reagents

Arkivoc

Volumn 2001, Issue 5, 2001, Pages 98-107

  Stavber, Stojan ^a   Jereb, Marjan ^a   Zupan, Marko ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

Alkoxylation; N fluoro diazonia compounds; Oxidation; p quinol derivatives; Phenols

Indexed keywords

1 FLUORO 4 CHLOROMETHYL 1,4 DIAZONIABICYCLO[2.2.2]OCTANE BIS(TETRAFLUOROBORATE); 2 FLUORO 4,6 DI TERT BUTYLPHENOL; 2,4,6 TRI TERT BUTYLPHENOL; ACETONITRILE; ALCOHOL; ALKADIENE; CATION; CYCLOHEXADIENONE; OCTANE; PHENOL; REAGENT; UNCLASSIFIED DRUG; WATER;

ARTICLE; HIGH TEMPERATURE PROCEDURES; LOW TEMPERATURE PROCEDURES; QUANTITATIVE ANALYSIS; SUBSTITUTION REACTION;

EID: 1642449010     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (35)

1. Banks, R.E.; Smart, B.E.; Tatlow, J.C., eds. Organofluorine Chemistry. Principles and Commercial Applications, Plenum Press: New York 1994;
2. a) Filler, R.; Kobayashi, Y.; Yagupolskii, L.M., eds. Organofluorine Compounds in Medicinal Chemistry and Biomedicinal Application, Elsevier: Amsterdam, 1993;
3. b) Hudlicky, M.; Pavlath, A.E. eds. Chemistry of Organic Fluorine Compounds II. A Critical Review, ACS Monograph 187; ACS, Washington DC, 1995.
4. c) Resnati, G.; Soloshnok, V.A., eds. Fluoroorganic Chemistry: Synthetic Challenges and Biomedicinal Rewards, Tetrahedron Symposia-in-Print No. 58, Tetrahedron, 1996, 52, 1-330;
5. d) Baasner, B.; Hagemann, H.; Tatlow, J.C., eds. Methods of Organic Chemistry (Houben-Weyl) Vol 10a and 10b: Organo-Fluorine Compounds. Thieme: New York 1999.
6. Lal, G.S.; Pez, G.P.; Syvret, R.G. Chem. Rev. 1996, 96, 1737.
7. Banks, R.E.; Mohialdin-Khaffaf, S.N.; Lal, S.G.; Sharif, I.; Syvret, R.G. J. Chem. Soc., Chem. Commun. 1992, 595.
8. a) Banks, R.E. J. Fluorine Chem. 1998, 87, 1;
9. b) Stavber, S.; Zupan, M. Tetrahedron Lett. 1996, 37, 3591;
10. c) Umemoto, T.; Nagayoshi, M. Bull. Chem. Soc. Jpn. 1996, 69, 2287.
11. a) Gilicinski, A.G.; Pez, G.P.; Syvret, R.G.; Lal, G.S. J. Fluorine Chem. 1992, 59, 157;
12. b) Differding, E.; Bersier, P.M. Tetrahedron 1992, 48, 1595.
13. a) Stavber, S.; Košir, I.; Zupan, M. J. Chem. Soc. Chem. Commun. 1992, 274;
14. b) Stavber, S.; Zupan, M. Tetrahedron Lett. 1993, 34, 4355;
15. c) Stavber, S.; Košir, I.; Zupan, M. J. Org. Chem. 1997, 62, 4916;
16. d) Zupan, M.; Iskra, J.; Stavber, S. Bull. Chem. Soc. Jpn. 1995, 68, 1655;
17. e) Stavber, S.; Zupan, M. Synlett 1996, 693;
18. f) Stavber, S.; Jereb, M.; Zupan, M. Synlett 1999, 1375.
19. Adler, E.; Andersson, G.; Edman, E. Acta Chem.Scand. B 29, 1975, 909.
20. McKillop, A.; McLaren, L.; Taylor, R.J.K. J. Chem. Soc. Perkin Trans. 1 1994, 2047.
21. a) Pelter, A.; Elgendy, S. Tetrahedron Lett. 1988, 29, 677;
22. b) Pelter, A.; Elgendy, S.M.A. J. Chem. Soc. Perkin Trans 1 1993, 1891.
23. McKillop, A.; Perry, D.H.; Edwards, M., Antus; S.; Farkas, L.; Nógrádi, M.; Taylor, E.C. J. Org. Chem. 1976, 41, 282.
24. Crandall, J.K.; Zucco, M.; Kirsch, R.S.; Coppert D.M. Tetrahedron Lett. 1991, 32, 5441.
25. Tashiro, M.; Yoshiya, H.; Fukata, G. J. Org. Chem. 1981, 46, 3784.
26. Dietl, H.; Young, H.S. J. Org. Chem. 1972, 37, 1672.
27. Capdevielle, P.; Maumy, M. Tetrahedron Lett. 1983, 24, 5611.
28. Homs, N.; de la Piscina, P.R.; Borrull, F. J. Chem. Soc. Chem. Commun. 1988, 1075.
29. a) Ronlan, A.; Parker, V.D. J. Chem. Soc. (C) 1971, 3214;
30. b) Nilsson, A.; Ronlan, A.; Parker, V.D.. J. Chem. Soc. Perkin Trans. 1 1973, 2337.
31. Eberson, L.; Hartshorn, M.P.; Radner, F.; Persson, O. J. Chem. Soc., Perkin Trans. 2 1998, 59.
32. Polishchuk, V.R.; German, L.S. Tetrahedron Lett. 1972, 51, 5169.
33. Tashiro, M.; Fukata, G. Heterocycles 1979, 12, 1551.
34. Tashiro, M.; Fukata, G.; Yoshiya, H. Synthesis 1979, 12, 988.
35. Quinkert, G.; Kleiner, E.; Freitag, B.J.; Glennberg, J.; Billhardt, U.M.; Cech, F.; Schmieder, K.R.; Schudok, C., Steinmetzer, H.C.; Bats, J.W., Zimmermann, G.; Dürner, G.; Rehm, D.; Paulus, E.F. Helv. Chem. Acta 1986, 69, 469.