Ring-opening reactions of diarylvinylidenecyclopropanes by iodine and bromine

Tetrahedron Letters

Volumn 46, Issue 44, 2005, Pages 7609-7613

  Shi, Min ^a   Ma, Ming ^a   Shao, Li Xiong ^b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Bromine; Diarylvinylidenecyclopropanes; Iodine; Naphthalene derivatives; Ring opening reaction

Indexed keywords

1,2 DICHLOROETHANE; BROMINE; CYCLOPROPANE DERIVATIVE; IODINE; NAPHTHALENE;

ARTICLE; BROMINATION; CHEMICAL REACTION; IODINATION; RING OPENING; TEMPERATURE;

EID: 26244450888     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.08.130     Document Type: Article

References (67)

1. M.L. Poutsma, and P.A. Ibarbia J. Am. Chem. Soc. 93 1971 440 450
2. W. Smadja Chem. Rev. 83 1983 263 320
3. D.R. Paulson, J.K. Crandall, and C.A. Bunnell J. Org. Chem. 35 1970 3708 3714
4. M.E. Hendrick, J.A. Hardie, and M. Jones Jr. J. Org. Chem. 36 1971 3061 3062
5. T.B. Patrick, E.C. Haynie, and W.J. Probst J. Org. Chem. 37 1972 1553 1556
6. D.H. Aue, and M.H. Meshishnek J. Am. Chem. Soc. 99 1977 223 231
7. T. Sasaki, S. Eguchi, and T. Ogawa J. Am. Chem. Soc. 97 1975 4413 4414
8. I.H. Sadler, and J.A.G. Stewart J. Chem. Soc., Perkin Trans. 2 1973 278 288
9. H. Sugita, K. Mizuno, T. Saito, K. Isagawa, and Y. Otsuji Tetrahedron Lett. 33 1992 2539 2542
10. K. Mizuno, H. Sugita, T. Kamada, and Y. Otsuji Chem. Lett. 1994 449 452
11. T. Akasaka, Y. Misawa, and W. Ando Tetrahedron Lett. 31 1990 1173 1176
12. K. Mizuno, H. Sugita, K. Isagawa, M. Goto, and Y. Otsuji Tetrahedron Lett. 34 1993 5737 5738
13. K. Mizuno, K. Nire, H. Sugita, and Y. Otsuji Tetrahedron Lett. 34 1993 6563 6566
14. K. Mizuno, H. Sugita, T. Hirai, and H. Maeda Chem. Lett. 2000 1144 1145
15. K. Mizuno, K. Nire, H. Sugita, and H. Maeda Tetrahedron Lett. 42 2001 2689 2692
16. K. Mizuno, H. Maeda, H. Sugita, S. Nishioka, T. Hirai, and A. Sugimoto Org. Lett. 3 2001 581 584
17. K. Mizuno, H. Sugita, T. Hirai, H. Maeda, Y. Otsuji, M. Yasuda, M. Hashiguchi, and K. Shima Tetrahedron Lett. 42 2001 3363 3366
18. H. Maeda, L. Zhen, T. Hirai, and K. Mizuno ITE Lett. Batteries, New Technol. Med. 3 2002 485 491
19. L.K. Sydnes Chem. Rev. 103 2003 1133 1150
20. For synthesis of vinylidenecyclopropanes, please see: K. Isagawa, K. Mizuno, H. Sugita, and Y. Otsuji J. Chem. Soc., Perkin Trans. 1 1991 2283 2285 and references cited therein
21. T. Sasaki, S. Eguchi, M. Ohno, and F. Nakata J. Org. Chem. 41 1976 2408 2411
22. T. Sasaki, S. Eguchi, and T. Ogawa J. Org. Chem. 39 1974 1927 1930
23. T. Sasaki, S. Eguchi, and T. Ogawa Heterocycles 3 1975 193 196
24. S. Eguchi, and M. Arasaki J. Chem. Soc., Perkin Trans. 1 1988 1047 1050
25. H. Sugita, K. Mizuno, T. Mori, K. Isagawa, and Y. Otsuji Angew. Chem., Int. Ed. Engl. 30 1991 984 986
26. T.B. Patrick Tetrahedron Lett. 15 1974 1407 1408
27. J.R. Al-Dulayymi, and M.S. Baird J. Chem. Soc., Perkin Trans. 1 1994 1547 1548
28. T.B. Patrick J. Org. Chem. 42 1977 3354 3356
29. H.D. Hartzler J. Am. Chem. Soc. 93 1971 4527 4531
30. The other papers related to vinylidenecyclopropanes. See: for the reactions of vinylidenecyclopropanes with carbenes and carbene complexes. J.K. Crandall, D.R. Paulson, and C.A. Bunnell Tetrahedron Lett. 1969 4217 4220
31. C.-C. Hwu, F.-C. Wang, and M.-C.P. Yeh J. Organomet. Chem. 474 1994 123 128
32. W.E. Billups, M.M. Haley, R. Boese, and D. Blaser Tetrahedron 50 1994 10693 10700
33. H. Maeda, T. Hirai, A. Sugimoto, and K. Mizuno J. Org. Chem. 68 2003 7700 7706
34. R. Bloch, P.L. Perchec, and J.-M. Conia Angew. Chem., Int. Ed. Engl. 9 1970 798 799
35. D.J. Pasto, and S.H. Yang J. Org. Chem. 51 1986 1676 1680
36. For the addition reactions to alkenylidenecyclopropanes. D.J. Pasto, and M.F. Miles J. Org. Chem. 41 1976 2608 2611
37. D.J. Pasto, A.F.-T. Chen, and G. Binsch J. Am. Chem. Soc. 95 1973 1553 1562
38. D.J. Pasto, and A.F.-T. Chen J. Am. Chem. Soc. 93 1971 2562 2564
39. D.J. Pasto, J.K. Borchardt, T.P. Fehlner, H.F. Baney, and M.E. Schwartz J. Am. Chem. Soc. 98 1976 526 529
40. D.J. Pasto, T.P. Fehlner, M.E. Schwartz, and H.F. Baney J. Am. Chem. Soc. 98 1976 530 534
41. D.J. Pasto, and M.F. Miles J. Org. Chem. 41 1976 425 432
42. D.J. Pasto, A.F.-T. Chen, G. Cuirdaru, and L.A. Paquette J. Org. Chem. 38 1973 1015 1026
43. R. Gompper, and D. Lach Tetrahedron Lett. 1973 2683 2686
44. R. Gompper, and D. Lach Tetrahedron Lett. 1973 2687 2690
45. D.J. Pasto, and D. Wampfler Tetrahedron Lett. 15 1974 1933 1936
46. D.J. Pasto, and J.L. Whitmer J. Org. Chem. 45 1980 1987 1990
47. D.J. Pasto, and J.E. Brophy J. Org. Chem. 56 1991 4556 4559
48. P.M. Cairns, L. Combie, and G. Pattenden Tetrahedron Lett. 23 1982 1405 1408
49. L. Combie, P.J. Maddocks, and G. Pattenden Tetrahedron Lett. 19 1978 3483 3486
50. G.-C. Xu, M. Ma, L.-P. Liu, and M. Shi Synlett 2005 1869 1872
51. 000 = 1072; Diffractometer: Rigaku AFC7R; Residuals: R; Rw: 0.0466, 0.1068.
52. L. Fitjer Angew. Chem., Int. Ed. Engl. 14 1975 360 361
53. H.-U. Siehl, and D.H. Aue Z. Rappoport P.J. Stang Dicoordinated Carbocations 1997 John Wiley & Sons New York 137 138
54. G.A. Olah, V.P. Reddy, and G.K.S. Prakash Chem. Rev. 92 1992 69 95
55. G.E. Heasley, D.A. Smith, J.N. Smith, V.L. Heasley, and D.F. Shellhamer J. Org. Chem. 45 1980 5206 5209
56. R.C. Fahey, and H.J. Schneider J. Am. Chem. Soc. 90 1968 4429 4434
57. C. Mioskowski Tetrahedron Lett. 35 1994 5437 5440
58. M. Iwaoka, H. Komatsu, T. Katsuda, and S. Tomoda J. Am. Chem. Soc. 126 2004 5309 5317
59. J.V. Comasseto, A.T. Omori, A.L.M. Porto, and L.H. Andrade Tetrahedron Lett. 45 2004 473 476
60. J. Oddershede, L. Henriksen, and S. Larsen Org. Biomol. Chem. 1 2003 1053 1060
61. B.C. Ranu, T. Mandal, and S. Samanta Org. Lett. 5 2003 1439 1441
62. M. Shi, L.-P. Liu, and J. Tang Org. Lett. 7 2005 3085 3088
63. R.F. Heck Acc. Chem. Res. 12 1979 146 151
64. H.A. Dieck, and R.F. Heck J. Am. Chem. Soc. 96 1974 1133 1136
65. R.F. Heck, and J.P. Nolley Jr. J. Org. Chem. 37 1972 2320 2322
66. J.E. Plevyak, and R.F. Heck J. Org. Chem. 43 1978 2454 2456
67. A.J. Chalk, and S.A. Magennis J. Org. Chem. 41 1976 273 278