The Fe0 promoted addition of CCl4 and CCl3Br to olefins

Synthetic Communications

Volumn 27, Issue 6, 1997, Pages 961-971

  Bellesia, Franco ^a   Forti, Luca ^a   Ghelfi, Franco ^a   Pagnoni, Ugo M ^a  

^a UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOBROMINE DERIVATIVE; ORGANOCHLORINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0030970156     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708003040     Document Type: Article

References (77)

1. a) Giese B., Ghosez A. and Zipse H., in Houben-Weil, Georg Thieme Verlag: Stuttgart, 1989, vol. E19a/2, 109 ff.
2. b) Unsin J. and Hemmer R., in Houben-Weil, Georg Thieme Verlag: Stuttgart, 1989, vol. E18, 1041 ff.
3. c) Walling C. and Huyser E. S., Organic Reaction, 1963, 13, 91.
4. a) Nesmeyanov A. N., Freidlina R. Kh., Kost V. N., Vassilyeva T. T. and Kopylova B. V., Tetrahedron, 1962, 17, 69.
5. b) Nesmeyanov A. N., Freidlina R. Kh. and Zakharkin L. I., Quart. Rev., 1956, 10, 330.
6. a) Kleschick W. A., Reed M. W. and Bordner J., J. Org. Chem., 1987, 52, 3168.
7. b) Belluš D., Pure & Appl. Chem., 1985, 57, 1827.
8. c) Martin P., Geuter H. and Belluš D., J. Am. Chem. Soc., 1979, 101, 5853.
9. d) Prakasa Rao A. S. C., Nayak U. R. and Dev S., Synthesis, 1975, 608.
10. e) Mc Fadden H. G., Harris R. L. N. and Jenkins C. L. D., Aust. J. Chem., 1989, 42, 301.
11. a) Kharasch M. S., Jensen E. V. and Urry W. H., J. Am. Chem. Soc., 1947, 69, 1100.
12. b) Kharasch M. S., Reinmuth O. and Urry W. H., ibid., 1947, 69, 1105;
13. c) Kooyman E. C. and Farennorst E., Rec. Trav. Chim., 1951, 69, 867.
14. a) Or(Orchov) A., Asscher M. and Vofsi D., J. Chem. Soc. Perkin Trans. II, 1973, 1000.
15. b) Asscher M. and Vofsi D., J. Chem. Soc. (B), 1968, 947.
16. c) Asscher M. and Vofsi D., ibid., 1963, 3921.
17. d) Asscher M. and Vofsi D., ibid., 1963, 1887.
18. a) Boutevin B., Furet Y., Lemanach L. and Vial-Reveillon F., J. Fluorine Chem., 1990, 47, 95.
19. b) Raynal S., Gautier J. C. and Christol F., Europ. Polym. J., 1979, 15, 311.
20. c) Pietrasanta Y. and Rigal G., C. R. Acad. Sc. Paris, 1972, 274, 2056.
21. d) Minisci F. and Galli R., Chimica e Industria (Milan), 1963, 45, 1401.
22. e) Minisci F. and Galli R., Tetrahedron Lett., 1962, 533.
23. a) Elzinga J. and Hogeveen H., J. Org. Chem., 1980, 45, 3957.
24. b) Freidlina R. Kh. and Chukovskaya E. C., Synthesis, 1974, 477.
25. c) Freidlina R. Kh. and Velicho F. K., Synthesis, 1977, 145.
26. a) Kamigata N. and Kameyama M., Yuki Gosei Kagaku Kyokaishi, 1989, 47, 436 (C. A., 1990, 112, 6852g)
27. a) Kamigata N. and Kameyama M., Yuki Gosei Kagaku Kyokaishi, 1989, 47, 436 (C. A., 1990, 112, 6852g)
28. b) Kameyama M. and Kamigata N., Bull. Chem. Soc. Jpn., 1987, 60, 3687.
29. c) Matsumoto H., Nakano T., Takasu K. and Nagai Y., J. Org. Chem., 1978, 43, 1734.
30. d) Matsumoto H., Nakano T. and Nagai Y., Tetrahedron Lett., 1973, 5147.
31. e) Grigg G., Devlin J., Ramasubbu A., Scott R. M. and Stevenson P., J. Chem. Soc. Perkin Trans. 1, 1987, 1515
32. f) Davis R., Furze J. D., Cole-Hamilton D. J. and Pogorzelec P., J. Organometal. Chem., 1992, 440, 191.
33. Tsuji J., Sato K. and Nagashima H., Tetrahedron, 1985, 41, 393.
34. a) Ma S. and Lu X., J. Chem. Soc. Perkin Trans. 1, 1990, 2031.
35. b) Khang S. K., Park C. H., Kim S. G. and Oh W. T., Bull. Korean Chem. Soc. 1991, 12, 716.
36. Mitani M., Kiriyama T. and Kuratate T., J. Org. Chem., 1994, 59, 1279.
37. Pereira S. and Srebnik M., J. Am Chem. Soc., 1996, 118, 909.
38. a) Van de Kuil L. A., Veldhuizen Y. S. J., Grove D. M., Zwikker J. W., Jenneskens L. W., Drenth W., Smeets W. J. J., Spek A. L. and van Koten G., Rec. Trav. Chim. Pays-Bas, 1994, 113, 267.
39. B) Saushkina T. P., Zubritskii L. M. and Petrov A. A., Zh. Org. Khim., 1980, 26, 722 (C. A., 1990, 113, 211319a).
40. B) Saushkina T. P., Zubritskii L. M. and Petrov A. A., Zh. Org. Khim., 1980, 26, 722 (C. A., 1990, 113, 211319a).
41. Maruoka K., Sano H., Fukutani Y. and Yamamoto H., Chem. Lett., 1985, 1689.
42. Davis R. and Groves F. I., J. Chem. Soc. Dalton Trans., 1982, 2281.
43. a) Helland B. R., Alvarez P. J. J. and Schnoor J. L., J. Hazard. Mater., 1995, 41, 205.
44. b) Warren, C. K., Arnold R. G., Bishop T. L., Lindholm L. C. and Betterton E. A., J. Hazard. Mater., 1995, 41, 217.
45. c) Matheson L. J. and Tratnyek P. G., Environ. Sci. Technol., 1994, 28, 2045.
46. a) Archer W. L. and Harter M. K., Corrosion, 1978, 34, 159.
47. b) Grunze M. and Dowben P. A., Appl. Surf. Sci., 1982, 10, 209.
48. c) for dissolution of iron in DMF by CC14 see: Lavrentiev I. P., Korableva L. G., Lavrentieva E. A., Ninfontova G. A., Khidekel M. L., Gusakovskaya I. G., Larkina T. I., Arutyunian L. D., Filipenko O. S., Ponomarev V. I. and Atovmyan L. O., Transition Met. Chem., 1980, 5, 193; and Garnovskii A. D., Kharisov B. I., Gojon-Zorilla G. and Garnovskii D. A., Russ. Chem. Rev., 1995, 64, 201.
49. c) for dissolution of iron in DMF by CC14 see: Lavrentiev I. P., Korableva L. G., Lavrentieva E. A., Ninfontova G. A., Khidekel M. L., Gusakovskaya I. G., Larkina T. I., Arutyunian L. D., Filipenko O. S., Ponomarev V. I. and Atovmyan L. O., Transition Met. Chem., 1980, 5, 193; and Garnovskii A. D., Kharisov B. I., Gojon-Zorilla G. and Garnovskii D. A., Russ. Chem. Rev., 1995, 64, 201.
50. Chen Q.-Y., He Y.-B. and Yang Z.-Y., J. Fluorine Chem., 1986, 34, 255.
51. a) Santford W. S., Eur. Pat. Appl. Ep. 131,561 (C. A., 1973, 103, 53693a).
52. b) Hoechst, Brit. 803,463 (C. A., 1959, 53, 11222b).
53. c) Qizhen G. and Weitho P., Huaxue Shiji, 1991, 13, 231.
54. d) Yusuke I. and Masato O., Japan Kokai 77,133,908 (C. A., 1978, 88, 152013m).
55. e) See also Karapet'yan Sh. A., Belyavskii A. B. and Kuz'mina N. A., Izv. Akad. Nauk SSSr, Ser. Khim., 1973, 6, 1272 (C. A., 1973, 79, 91497n); Chang C. C., Yang S. L. and Chang C. T., J. Chin. Chem. Soc. (Taipei), 1988, 35, 321; and, Davis R., Khazaal N. M. S. and Maistry V., J. Chem. Soc. Chem. Commun., 1986, 1387.
56. e) See also Karapet'yan Sh. A., Belyavskii A. B. and Kuz'mina N. A., Izv. Akad. Nauk SSSr, Ser. Khim., 1973, 6, 1272 (C. A., 1973, 79, 91497n); Chang C. C., Yang S. L. and Chang C. T., J. Chin. Chem. Soc. (Taipei), 1988, 35, 321; and, Davis R., Khazaal N. M. S. and Maistry V., J. Chem. Soc. Chem. Commun., 1986, 1387.
57. e) See also Karapet'yan Sh. A., Belyavskii A. B. and Kuz'mina N. A., Izv. Akad. Nauk SSSr, Ser. Khim., 1973, 6, 1272 (C. A., 1973, 79, 91497n); Chang C. C., Yang S. L. and Chang C. T., J. Chin. Chem. Soc. (Taipei), 1988, 35, 321; and, Davis R., Khazaal N. M. S. and Maistry V., J. Chem. Soc. Chem. Commun., 1986, 1387.
58. e) See also Karapet'yan Sh. A., Belyavskii A. B. and Kuz'mina N. A., Izv. Akad. Nauk SSSr, Ser. Khim., 1973, 6, 1272 (C. A., 1973, 79, 91497n); Chang C. C., Yang S. L. and Chang C. T., J. Chin. Chem. Soc. (Taipei), 1988, 35, 321; and, Davis R., Khazaal N. M. S. and Maistry V., J. Chem. Soc. Chem. Commun., 1986, 1387.
59. Forti L., Ghelfi F., Lodi Lancellotti M. and Pagnoni U. M., Synth. Commun., 1996, 26, 1699.
60. 4b as initiators in radical halo-alkyl-additions with polyhalomethanes has been reported.
61. a) Terent'ev A. B. and Vasil'eva T. T., Russ. Chem. Rev., 1994, 63, 269.
62. b) Timokhin B. V., Russ. Chem. Rev., 1990, 59, 193.
63. Huyser E. S., J. Org. Chem., 1961, 26, 3261; Brace N. O., ibid., 1963, 28, 3093.
64. Huyser E. S., J. Org. Chem., 1961, 26, 3261; Brace N. O., ibid., 1963, 28, 3093.
65. a) Davis R., Stephens K. and Háyek M., J. Mol. Cat., 1994, 92, 269.
66. 4-Octyne, an internal alkyne, gives some higher conversion than 1-octyne, but the main product derives from an unexpected HCl addition to the triple bond.
67. Heiba E. I. and Dessau R. M., J. Am. Chem. Soc., 1967, 89, 3772. For a different point of view, see Kharasch M. S., Jerome J. J. and Urry W. H., J. Org. Chem., 1950, 15, 966.
68. Heiba E. I. and Dessau R. M., J. Am. Chem. Soc., 1967, 89, 3772. For a different point of view, see Kharasch M. S., Jerome J. J. and Urry W. H., J. Org. Chem., 1950, 15, 966.
69. Forti L., Ghelfi F. and Pagnoni U. M., unpublished results.
70. High headspaces negatively affect the reaction, owing to the partition of olefin and polyhalomethane between liquid and vapour phases. The best yields are obtained on working with Schlenk capacity little higher than the reaction volume.
71. a) Martin M. M. and Gleycher G. J., J. Am. Chem. Soc., 1964, 86, 233.
72. b) Quelet R. and Durand-Dran R., Compt. Rend. Acad. Sci. Ser. C, 1958, 246, 774.
73. Kondakov S. R. and Smirnov V. V., Kinet. Catal., 1995, 36, 315.
74. Kondakov S. R., Smirnov V. V. and Zagorski, V. V., Vestn. Mosk. Univ., Ser. 2: Khim., 1991, 32, 140 (C. A., 1991, 115, 196768s).
75. Kondakov S. R., Smirnov V. V. and Zagorski, V. V., Vestn. Mosk. Univ., Ser. 2: Khim., 1991, 32, 140 (C. A., 1991, 115, 196768s).
76. a) Hàjek M. and Silhavy P., Czech. Cs 275,585 (C. A., 1993, 119, 225670u).
77. b) Decker D. L., Moore C. and Tousignant W. F., U.S. 3,862,978 (C. A., 1975, 82, 125048w).