A rapid, mild and acid-free procedure for the preparation of acyl chlorides including formyl chloride

Tetrahedron Letters

Volumn 38, Issue 37, 1997, Pages 6489-6492

  Villeneuve, G B ^a   Chan, T H ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; CHLORINATED HYDROCARBON; DICHLOROMETHANE; FORMIC ACID; PHOSPHINE DERIVATIVE;

ARTICLE; SYNTHESIS;

EID: 0030848431     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01511-6     Document Type: Article

References (18)

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2. Shiori, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203-6205.
3. Belleau, B.; Malek, G. J. Am. Chem. Soc. 1968, 90, 1651-1652.
4. Palomo, A. L.; Cabré, J. Synthesis, 1984, 413-417.
5. Olah, G. A.; Nojima, M.; Kerekes, I. Synthesis, 1973, 487-488.
6. Lee, J. B. J. Am. Chem. Soc. 1966, 88, 3440-3441.
7. For a review see: Appel, R. Angew. Chem. Int Ed. Engl. 1975, 12, 801-811. For the original paper see: Crofts, P. C.; Downie, I. M. J. Chem. Soc. 1963, 2559-2560.
8. For a review see: Appel, R. Angew. Chem. Int Ed. Engl. 1975, 12, 801-811. For the original paper see: Crofts, P. C.; Downie, I. M. J. Chem. Soc. 1963, 2559-2560.
9. Venkataraman, K.; Wagle, D. R. Tetrahedron. Lett. 1979, 3037-3040.
10. Devos, A. ; Remion, J.; Frisque-Hesbain, A. M.; Colens, A.; Ghosez, L. J. Chem. Soc. Chem. Comm. 1979, 1180-1181.
11. Haveux, B.; Dekoker, A.; Rens, M.; Sidani, A. R.; Toye, J.; Ghosez, L. Org. Synth. 1979, 59, 26-34.
12. Magid, R. M.; Fruchey, O. S.; Johnson, W. L. ; Allen, T. G. J. Org. Chem. 1979, 44, 359-363.
13. We already knew at that point that we had formed the acyl chloride and not the anhydride since the anhydride, obtained with the reagent BOPCl, proved unable to react with 2 in pyridine at room temperature.
14. Panetta, C. A.; Casanova, T. G. J. Org. Chem. 1970, 35, 2423-2425.
15. Benzoyl chloride moved well without decomposing on TLC, and therefore its formation from benzoic acid was easily assessed. On the other hand, the acyl chloride of carboxylic acid 1 decomposed on TLC.
16. It has already been reported that anhydrides of carboxylic acids can be formed with a stoichiometric amount of hexamethylphosporane triamine and carbon tetrachloride at -78 °C. Casto, B.; Doromoy, J. R. Bull. Soc. Chim. Fr. 1971, 8, 3034-3036.
17. Staab, H. A.; Datta, A. P. Angew. Chem. Int. Ed. Engl.1964, 3, 132.
18. Formic acid 98-100 % from American Chemicals Ltd. (Montréal) was used as supplied. The latter froze when kept at 5 °C for 24 h. Lower grade formic acid did not give rise to the desired reaction.