Triflic acid an efficient catalyst for the Thiele-Winter reaction

Tetrahedron Letters

Volumn 38, Issue 27, 1997, Pages 4777-4778

  Villemin, Didier ^a   Bar, Nathalie ^a   Hammadi, Mohamed ^b  

^a UNIVERSITÉ DE CAEN   (France)

^b UNIVERSITY OF BOUMERDES   (Algeria)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ANHYDRIDE; INORGANIC ACID; QUINONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; REACTION ANALYSIS;

EID: 0030987390     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01049-6     Document Type: Article

References (11)

1. Thiele, J. Ber, 1898, 31, 1247-1249.
2. Thiele, J.; Winter, E. Ann, 1900, 311, 341-352.
3. Mc Omie, J.F.W.; Blatchley, J.M. Org. React., 1972, 19, 199-277.
4. Fieser, L. J. Amer. Chem. Soc., 1948, 70, 3165-3174.
5. Burton, H.; Praill, P.J.G. J. Chem. Soc., 1952, 755-759.
6. Fieser, L. ; Fieser, M., Advanced Organic Chemistry, Reinhold, New York 2nd ed., 1962, 855-856.
7. Hammadi, M., Ph D thesis, Caen 1996.
8. For example, menadione ( 10 mmol) in acetic anhydride (0.2 mol) and triflic acid (5 mmol) was stirred at room temperature for 20 h. The mixture was poured on ice and filtered. The triacetate was crystallised from methanol. All triacetates showed correct, PMR, CMR, IR, mass spectra and elemental analyses (C,H).
9. Howells, R.D.; Mc Cown, J.D., Chem. Rev., 1977, 77, 69-92; Stang, P.J.; White, M.R., Aldrichimica Acta, 1983, 16, 15-22; Encyclopedia of Reagents for Organic Synthesis, Paquette, L.A. editor, J. Wiley and Sons, Chichester, 1995, 5143-5146.
10. Howells, R.D.; Mc Cown, J.D., Chem. Rev., 1977, 77, 69-92; Stang, P.J.; White, M.R., Aldrichimica Acta, 1983, 16, 15-22; Encyclopedia of Reagents for Organic Synthesis, Paquette, L.A. editor, J. Wiley and Sons, Chichester, 1995, 5143-5146.
11. Howells, R.D.; Mc Cown, J.D., Chem. Rev., 1977, 77, 69-92; Stang, P.J.; White, M.R., Aldrichimica Acta, 1983, 16, 15-22; Encyclopedia of Reagents for Organic Synthesis, Paquette, L.A. editor, J. Wiley and Sons, Chichester, 1995, 5143-5146.