Liquid-Phase Decarboxylation of Aromatic Haloformates: A New Access to Chloro- and Fluoroaromatics

Journal of Organic Chemistry

Volumn 63, Issue 8, 1998, Pages 2493-2496

  Lui, Norbert ^a   Marhold, Albrecht ^a   Rock, Michael H ^a  

^a BAYER AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542606496     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9716486     Document Type: Article

References (44)

1. Backer, A. Inventory of Industrial Fluoro- Biochemicals; Editions Eyrolles: Paris, 1996.
2. Houben-Weyl, Methoden der Organischen Chemie band V/3; Georg Thieme Verlag: Stuttgart, 1962.
3. Harthman, W. W.; Berthen, M. R. Org. Synth. 1955, 3, 79-81.
4. Hudlicky, M. Chemistry of Organic Fluorine Compounds, John Wiley & Sons: New York, 1976; pp 46-48.
5. Langlois, B.; Gilbert, L.; Forat, G. Ind. Chem. Libr. 1996, 8, 244-291.
6. (a) Balz, G.; Schiemann, G. Chem. Ber. 1927, 60, 1186-1190.
7. (b) Osswald, P. Scherer, German Patent 600, 706, 1934.
8. (c) Fern, R. L.; Vander Werf, C. A. J. Am. Chem. Soc. 1950, 72, 4809-4811.
9. (a) Weickmann, A. German Patent 857,350, 1949.
10. (b) Eilingsfeld, H.; Seefelder, M.; Weidiner, H. Angew. Chem. 1960, 72, 836-845.
11. (c) Nakanisihi, S.; Myers, T. C. Jensen J. Am. Chem. Soc. 1955, 77, 3099-3100.
12. (d) Nakanisihi, S.; Myers, T. C. Jensen J. Am. Chem. Soc. 1955, 77, 5033-5034.
13. (e) US Patent 4,814,524, 1989.
14. (f) Clinch, P. W.; Hudson, H. R. J. Chem. Soc. B 1971, 747-745.
15. (a) Christe, K. O.; Pavlath, A. E. J. Org. Chem. 1965, 30, 3170-3173.
16. (b) Christe, K. O.; Pavlath, A. E. J. Org. Chem. 1965, 30, 4104-4107.
17. (c) Christe, K. O.; Pavlath, A. E. J. Org. Chem. 1966, 31, 559-561.
18. (d) Christe, K. O.; Pavlath, A. E. U.S. Patent 3,283,018, 1966.
19. (a) Aston, D. P.; Ryan, A.; Webster, B. F.; Wolfindale, B. A. J. Fluorine Chem. 1985, 263-274.
20. (b) Aston, D. P.; Ryan, A.; Webster, B. F.; Wolfindale, B. A. European Patent 0,118,241, 1984.
21. (c) Aston, D. P.; Ryan, A.; Webster, B. F.; Wolfindale, B. A. U.S. Patent 4,745,235.
22. Garcia, H.; Gilbert, L.; Perrod, M. C.; Ratton, S.; Rochin, C. Ind. Chem. Libr. 1996, 8, 301-312.
23. (a) Lui, N.; Bielefeldt, D.; Marhold, A. U.S. Patent US 5,306,849, 1994.
24. (b) Lui, N.; Marhold. A. German Patent DEA 4415777.
25. (c) Lui, N. Rock, M. H. German Patent DEA 19642868.
26. Olah, G. A. Friedel - Crafts and related reactions; Interscience Publishers: New York, 1963; Vol. 1.
27. Coppock, W. H. J. Org. Chem. 1957, 22, 325-326.
28. Dang, V. A.; Olofson, R. A. J. Org. Chem. 1990, 55, 1847-1851
29. (a) Pattison, V. A.; Colson, J. G.; Carr, R. L. K. J. Org. Chem. 1968, 33, 1084-1087.
30. (b) Zabik, M. J.; Schuetz, R. D. J. Org. Chem. 1967, 32, 300-307.
31. (c) Pickard, R. H.; Littlebury, W. O. J. Chem. Soc. 1907, 91, 302-307.
32. (d) Barnes, J. H. J. Pharm. Pharmacol. 1961, 13, 39-48.
33. (e) Altner, W.; Meisert, E.; Rockstroh, G. German Patent 1,117,589, 1961; Chem. Abstr. 1962, 57, 11106d.
34. (e) Altner, W.; Meisert, E.; Rockstroh, G. German Patent 1,117,589, 1961; Chem. Abstr. 1962, 57, 11106d.
35. (a) Jenneskens, L. W.; De Wolf, W. H.; Bickelhaupt, F. Synthesis 1985, 647-649.
36. (b) Brown, F.; Bruyne, J. M. A.; Gross, P. J. Am. Chem. Soc. 1934, 56, 1-93.
37. (c) Socrates, G.; Adlard, M. W. J. Chem. Soc B, 1971, 733-736.
38. (d) Hopff, H.; Gallegra, P. Helv. Chim. Acta 1968, 51, 253-260.
39. (e) Beak, P.; Trancik, R. J.; Simpson, D. A. J. Am. Chem. Soc. 1969, 91, 5073-5086.
40. (a) Nasir, M. S.; Cohen, I. C.; Karlin, K. D. J. Am. Chem. Soc. 1992, 114, 2482-2494.
41. (b) De Meio, G.; Morgen, J.; Pinhey, J. T. Tetrahedron 1993, 49, 8129-8139.
42. (c) Schieh, T. C.; Feit, E. D.; Chernick, C. L.; Yang, N. C. J. Org. Chem. 1967, 32, 300-307.
43. (d) Sket, B.; Zupan, M. J. Org. Chem. 1978, 43, 835-837.
44. Fountain, K. R.; Pierschbacher, M. J. Org. Chem. 1976, 41, 2039-2042.