Hydrodehalogenation of 1,1-dibromocyclopropanes by Grignard reagents promoted by titanium compounds

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 7, 2000, Pages 1603-1617

  Al Dulayymi, Juma'a R ^a   Baird, Mark S ^a   Bolesov, Ivan G ^a   Nizovtsev, Alexey V ^a   Tverezovsky, Viacheslav V ^a  

^a BANGOR UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AGENTS; CATALYSTS; COMPOSITION EFFECTS; DEHALOGENATION; DIMERIZATION; HYDROGENATION; THERMAL EFFECTS; TITANIUM COMPOUNDS;

DIBROMOCYCLOPROPANES; ETHYMAGNESIUM BROMIDE; GRIGNARD REAGENTS; HYDRODEHALOGENATION; HYDROGEN ABSTRACTION; ISOPROPOXIDE;

BROMINE COMPOUNDS;

EID: 0034236762     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a910317l     Document Type: Article

References (126)

1. E. V. Dehmlow, Houben-Weyl, Methods Org. Chem., 1989, E 19b, 1600.
2. A. Jonczyk and M. Fedorynski, Houben-Weyl, Methods Org. Chem., 1997, E 17a, 533.
3. P Weyerstahl, The Chemistry of The Carbon-Halogen Bond, in The Chemistry of Functional Groups, Suppl. D, Ed. S. Patai and Z. Rappoport, Wiley, New York, 1983, p. 1451,
4. R. R. Kostikov, A. P. Molchanov and H. Hopf, Top. Curr. Chem., 1990, 155, 41.
5. (a) D. Seyferth, H. Yamazaki and D. L. Alleston, J. Org. Chem., 1963, 28, 703
6. (b) E. Vogel, W. Grimme and S. Korte, Tetrahedron Lett., 1965, 3625
7. (c) J. Meinwald, J. W. Wheeler, A. A. Nimetz and J. S. Liu, J. Org. Chem. 1965, 30, 1038
8. (d) G. Schrumpf and W. Lüttke, Liebigs Ann. Chem. 1969, 730, 100
9. (e) L. K. Sydnes, Acta Chem. Scand., Ser. B, 1978, 32, 47
10. (f) J. A. Landgrebe and L. W. Becker, J. Org. Chem., 1968, 33, 1173
11. (g) H. M. Walborsky, Tetrahedron, 1981, 37, 1625.
12. H. Yamanaka, R. Oshima, K. Teramura and T. Ando, J. Org. Chem., 1972, 37, 1734.
13. N. I. Yakushkina, G. A. Zakharova, L. S. Surmina and I. G. Bolesov, Zh. Org. Khim., 1980, 16, 1834.
14. R. M. Blankenship, K. A. Burdett and J. S. Swenton, J. Org. Chem., 1974, 39, 2300.
15. C. L. Osborn, T. C. Shields, B. A. Shoulders, J. F. Krause, H. V. Cortez and P. D. Gardner, J. Am. Chem. Soc., 1965, 87, 3158.
16. K. Hofmann, S. F. Orochena, S. M. Sax and G. A. Jeffrey, J. Am. Chem. Soc., 1959, 81, 992
17. J. A. Landgrebe and D. E. Applequist, J. Am. Chem. Soc., 1964, 86, 1536
18. M. S. Baird and C. B. Reese, Chem. Commun., 1970, 1519.
19. K. Oshima, T. Shirafuji, H. Yamamoto and H. Nozaki, Bull. Chem. Soc. Jpn., 1973, 46, 1233.
20. N. Shimizu and S. Nishida, Chem. Lett., 1977, 839.
21. A. J. Fry and R. H. Moore, J. Org. Chem., 1968, 33, 1283.
22. R. E. Erickson, R. Annino, M. D. Scanlon and G. Zon, J. Am. Chem. Soc., 1969, 91, 1767.
23. L. K. Sydnes and L. Skattebol, Acta Chem. Scand., Ser. B, 1978, 32, 632.
24. J. D. White and L. G. Wade, J. Org. Chem., 1975, 40, 118.
25. K. Isagai and I. Kasama, Nippon Kagaku Zasshi, 1967, 88, 106
26. K. Isagai and S. Kondo, Nippon Kagaku Zasshi, 1968, 89, 97
27. K. Hofmann, S. F. Orochena, S. M. Max and G. A. Jeffrey, J. Am. Chem. Soc., 1959, 81, 992
28. W. Schwarze, A. Klemann and W. Leuchtenberger, Eur. Pat. Appl. EP EP 43950
29. W. Schwarze, A. Klemann and W. Leuchtenberger, Chem. Abstr., 1982, 96, 180856x
30. H. J. Birch, G. M. Iskander, B. I. Magboul and F. Stansfield, J. Chem. Soc. (C), 1967, 358.
31. C. L. Osborn, T. C. Shields, B. A. Shoulders, C. G. Cardenas and P. D. Gardner, Chem. Ind. (London), 1965, 766
32. G. W. Wijsman, W. H. de Wolf and F. Bickelhaupt, Recl. Trav. Chim. Pays-Bas, 1994, 113, 53.
33. T. Hirao, K. Hirano, T. Hasegawa, Y. Ohshiro and I. Ikeda, J. Org. Khim., 1993, 58, 6529.
34. O. G. Kulinkovich, S. V. Sviridov, D. A. Vasilevski and T. S. Pritytskaya, Zh. Org. Khim., 1989, 25, 2244
35. O. G. Kulinkovich, S. V. Sviridov and D. A. Vasilevski, Synthesis, 1991, 234.
36. J. R. Al Dulayymi, M. S. Baird, I. G. Bolesov, V. Tverezovsky and M. Rubin, Tetrahedron Lett., 1996, 37, 8933.
37. (a) N. I. Yakushkina and I. G. Bolesov, Zh. Org. Khim., 1979, 15, 954
38. (b) N. V. Bovin, L. S. Surmina, N. I. Yakushkina and I. G. Bolesov, Zh. Org. Khim., 1977, 13, 1888.
39. W. E. Billups, L. E. Reed and E. W. Casserly, J. Org. Chem., 1981, 46, 1326
40. B. Halton and D. L. Officer, Tetrahedron Lett., 1981, 3687
41. R. H. Parker and W. M. Jones, Tetrahedron Lett., 1984, 1245;
42. O. G. Kulinkovich, I. G. Tishchenko and Y. N. Romashin, Zh. Org. Khim., 1985, 21, 90.
43. E. V. Dehmlow and H. Lustinetz, Liebigs Ann. Chem., 1996, 2065.
44. M. S. Baird and H. H. Hussain, unpublished results.
45. A. R. Al Dulayymi and M. S. Baird, J. Chem. Soc., Perkin Trans. 1, 1994, 1547.
46. K. Kitatani, T. Hiyama and H. Nozaki, Bull. Chem. Soc. Jpn., 1977, 50, 3288.
47. G. F. Meijs and I. R. Doyle, J. Org. Chem., 1985, 50, 3713.
48. See ref. 4g
49. T. Ando, H. Hosaka, W. Funasaka and H. Yamanaka, Bull. Chem. Soc. Jpn., 1973, 46, 3513.
50. See ref. 4e.
51. T. Harada, K. Hattori, T. Katsuhira and A. Oku, Tetrahedron Lett., 1989, 6035.
52. C. W. Jefford, D. Kirkpatrick and F. Delay, J. Am. Chem. Soc., 1972, 94, 8905.
53. N. Shimizu, K. Watanabe and Y. Tsuno, Chem. Lett., 1983, 1877.
54. A. I. D'yachenko, O. S. Korneva, N. M. Abramova and O. M. Nefedov, Izv. Akad. Nauk USSR, Ser. Khim., 1984, 2818.
55. T. Shirafuji, K. Oshima, Y. Yamamoto and H. Nozaki, Bull. Chem. Soc. Jpn. 1971, 44, 3161.
56. N. Shimizu, K. Watanabe and Y. Tsuno, Bull. Chem. Soc. Jpn., 1984, 57, 885.
57. U. M. Djemilev and R. L. Gaisin, Izv. Akad. Nauk USSR, Ser. Khim., 2332.
58. V. F. Dovganyuk, V. Z. Sharf, L. G. Saginova, I. I. Antokol'skaya and L. I. Bol'shakova, Izv. Akad. Nauk USSR, Ser. Khim., 1989, 777.
59. T. Hirao, T. Masunaga, Y. Ohshiro and T. Agawa, J. Org. Chem., 1981, 46, 3745.
60. Y. Tanabe, K.-I. Wakimura and Y. Nishii, Tetrahedron Lett., 1996, 1837.
61. J. Backes and U. H. Brinker, Houben-Weyl, Methods Org. Chem., E 19b, 407
62. H. E. Schuster and G. M. Coppola, Allenes in Organic Synthesis, Wiley-International, New York, 1984
63. S. R. Landor, The Chemistry of the Allene, Academic Press, New York, 1982, vols. 1-3.
64. M. S. Baird, I. G. Bolesov, M. A. Rubin, V. V. Tverezovsky and Ai P. Yang, unpublished results.
65. D. Seyferth and B. Prokai, J. Org. Chem., 1966, 31, 1702
66. D. Seyferth and R. M. Lambert, J. Organomet. Chem., 1975, 88, 287
67. O. M. Nefedov and E. S. Agavelyan, Izv. Akad. Nauk USSR, Ser. Khim., 1974, 838.
68. F. W. Frey, J. Org. Chem., 1961, 26, 5187.
69. W. B. Smith, J. Org. Chem., 1961, 26, 4206.
70. D. I. Davies, J. N. Done and D. H. Hey, J. Chem. Soc. (C), 1969, 2506
71. J. Chem. Soc. (C), 1963, 1392
72. D. I. Davies, D. H. Hey and M. Triecco, J. Chem. Soc. (C), 1965, 7062.
73. R. O. C. Norman and W. A. Waters, J. Chem. Soc., 1957, 950.
74. Y. Nishii, K. Wakasugi and Y. Tanabe, Synlett, 1998, 67.
75. D. I. Davies, J. W. Dove and D. H. Hey, J. Chem. Soc. (C), 1969, 2506
76. I. U. Khand, P. L. Pauson and W. E. Watts, J. Chem. Soc. (C), 1969 2021.
77. M. H. Abraham and M. J. Hogarth, J. Organomet. Chem., 1968, 12, 497.
78. M. Tamura and J. Kochi, J. Am. Chem. Soc., 1971, 93, 1485
79. K. Wada, M. Tamura and J. Kochi, J. Am. Chem. Soc., 1970, 92, 6656
80. M. Tamura and J. Kochi, Synthesis, 1971, 303.
81. J. J. Eisch, X. Shi, J. R. Alila and S. Thiele, Chem. Ber., 1997, 130, 1175.
82. M. S. Baird, I. G. Bolesov and A. V. Nizovtsev, unpulibshed results.
83. Z. Bregar, S. Stavber and M. Zupar, J. Fluorine Chem., 1989, 44, 187.
84. H. Ishikawa, T. Mukaiyama and S. Ikeda, Bull. Chem. Soc. Jpn., 1981, 54, 776.
85. P. R. Sharan, P. Smith and W. A. Waters, J. Chem. Soc. (B), 1968, 1322.
86. W. H. Urry and M. S. Kharasch, J. Am. Chem. Soc., 1944, 66, 1438.
87. S. S. Hall, J. Org. Chem., 1973, 38, 1738.
88. D. Pasto and G. L'Hermine, Tetrahedron, 1993, 49, 3259.
89. L. A. Paquette and R. F. Eizember, J. Am. Chem. Soc., 1969, 91, 7108.
90. C. Hamdouchi, M. Topolski, V. Goedken and H. M. Walborsky, J. Org. Chem., 1993, 58, 3148.
91. B. Bogdanovich, K. Schlichte and U. Westeppe, Chem. Ber., 1988, 121, 27.
92. J. J. Eisch, X. Shi, J. R. Alila and S. Thiele, Chem. Ber., 1997, 130, 1175
93. J. J. Eisch, X. Shi and J. Lasota, Z. Naturforsch. Teil B, 1995, 50, 342
94. H. Gilman and R. G. Jones, J. Org. Chem., 1945, 10, 505.
95. W. J. Dale and P. E. Swartzentruber, J. Org. Chem., 1959, 24, 955.
96. T. Ando, T. Muranaka and T. Ishihara, Bull. Chem. Soc. Jpn., 1981, 54, 3227
97. G. F. Meijs, J. Org. Chem., 1984, 3863.
98. See ref. 13.
99. T. Asahara, K. Ono and K. Tanaka, Bull. Chem. Soc. Jpn., 1971, 44, 1130.
100. R. R. Kostikov and A. P. Molchanov, J. Org. Chem. USSR (Engl. Transl.), 1975, 11, 1871.
101. H.-J. Pyun, R. M. Coates, K. C. Wagschal, P. McGeady and R. B. Croteau, J. Org. Chem., 1993, 58, 3998.
102. M. S. Baird, W. Nethercott and P. D. Slowey, J. Chem. Res. Miniprint, 1985, 12, 3815.
103. S. A. Stein and T. H. Morton, Tetrahedron Lett., 1973, 4933.
104. T. Shirafuji, K. Ochima, Y. Yamamoto and H. Nozaki, Bull. Chem. Soc. Jpn., 1971, 44, 3161
105. G. Guillaumet, L. Mordenti and P. Caubere, J. Organomet. Chem., 1975, 102, 353.
106. J. F. Garst, F. Ungváry, R. Batlaw and K. E. Lawrence, J. Am. Chem. Soc., 1991, 113, 5397.
107. E. H. White, K. W. Field, W. H. Hendrickson, P. Dradzic, D. F. Roswell and P. W. Mullen, J. Am. Chem. Soc., 1992, 114, 8023
108. P. C. H. Etlinger, J. H. Bowie and T. Blumenthal, J. Org. Chem., 1986, 51, 5078
109. S. Kim, K. N. Cheung and S. Yang, J. Org. Chem., 1987, 52, 3917.
110. H. M. Walborsky and M. S. Aronoff, J. Organomet. Chem., 1973, 51, 31.
111. H. W. J. J. Bodewitz, B. J. Schaart, J. D. Van der Niet, C. Blomberg, F. Bickelhaupt and J. A. den Hollander, Tetrahedron, 1978, 34, 2523
112. Z. Chami, M. Gareil, J. Pinson, J.-M. Saveant and A. Theibault, J. Org. Chem., 1991, 56, 586.
113. D. R. Arnold and S. A. Mines, Can. J. Chem., 1989, 67, 689.
114. H. Ishikawa, T. Mukaiyama and S. Ikeda, Bull. Chem. Soc. Jpn., 1981, 54, 776.
115. W. Carpenter, A. M. Duffield and C. Djerassi, J. Am. Chem. Soc., 1967, 89, 6167
116. J. C. Traeger, C. E. Hudson and D. J. McAdoo, J. Phys. Chem., 1990, 94 5714.
117. S. H. Goh, L. E. Closs and G. L. Closs, J. Org. Chem., 1969, 34, 25
118. H. Tomioka, Y. Ozaki and Y. Izawa, Tetrahedron, 1985, 41, 4987.
119. L. K. Sydnes and S. Skare, Can. J. Chem., 1984, 62, 2073.
120. M. S. Baird, P. Licence, V. V. Tverezovsky and I. G. Bolesov, Tetrahedron, 1999, 55, 2773.
121. C. Delseth and J.-P. Kitzinger, Helv. Chim. Acta, 1978, 61, 1327.
122. L. A. Farley, J. C. Lee, R. H. Crabtree and P. E. M. Siegbahn, J. Organomet. Chem., 1995, 504, 57.
123. E. E. van Tamalen, J. I. Brauman and L. E. Ellis, J. Am. Chem. Soc., 1971, 93, 6141
124. C. Delseth and J.-P. Kintzinger, Helv. Chim. Acta, 1978, 61, 1327
125. R. D. Bowen and A. Macoll, J. Chem. Soc., Perkin Trans. 2, 1990, 147.
126. M. S. Baird, P. Licence, V. V. Tverezovsky, I. G. Bolesov and W. Clegg, Tetrahedron, 1999, 55, 2784.