Ring-opening reactions of arylvinylidenecyclopropanes with diaryl diselenide upon heating: Formation of 1,2-diarylselenocyclopentene derivatives

Tetrahedron Letters

Volumn 46, Issue 28, 2005, Pages 4745-4748

  Shi, Min ^a   Lu, Jian Mei ^a   Xu, Guang Cai ^b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

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

Author keywords

Arylvinylidenecyclopropanes; Cyclopentene derivatives; Diaryl diselenides; Heating

Indexed keywords

CYCLOPENTENE DERIVATIVE; CYCLOPROPANE DERIVATIVE; SELENIDE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; HEATING; QUANTUM YIELD; RING OPENING;

EID: 20444412665     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.05.029     Document Type: Article

References (69)

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 2 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. 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. 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. A. Ogawa, N. Takami, M. Sekiguchi, H. Yokoyama, H. Kuniyasu, I. Ryu, and N. Sonoda Chem. Lett. 1991 2241 2242
51. L.-P. Liu, and M. Shi Chem. Commun. 2004 2878 2879
52. 000 = 1224; Diffractometer: Rigaku AFC7R; Residuals: R; Rw: 0.0352, 0.0779
53. L. Henriksen S.J. Patai The Chemistry of Organic Selenium and Tellurium Compounds Vol. 2 1987 Wiley-Interscience New York Chapter 10
54. T. Hirabayashi, S. Mohmand, and H. Bock Chem. Ber. 115 1982 483 491
55. J.Y.C. Chu, and J.W. Lewichi J. Org. Chem. 42 1977 2491 2493
56. J.K. Kochi, P.J. Krusic, and D.R. Eaton J. Am. Chem. Soc. 91 1969 1877 1879
57. L. Mathew, and J. Warkentin J. Am. Chem. Soc. 108 1986 7981 7984
58. V.W. Bowry, J. Lusztyk, and K.U. Ingold J. Am. Chem. Soc. 113 1991 5687 5688
59. A.L.J. Beckwith, and V.W. Bowry J. Am. Chem. Soc. 116 1994 2710 2716
60. J. Masnovi, E.G. Samsel, and R.M. Bullock Chem. Commun. 1989 1044 1045
61. H. Okamura, M. Miura, K. Kosugi, and H. Takei Tetrahedron Lett. 21 1980 87 90
62. A.V. Martynov, V.A. Potapov, S.V. Amosova, N.A. Makhaeva, I.P. Beletskaya, and L. Hevesi J. Organomet. Chem. 674 2003 101 103
63. C.C. Silveira, P.C.S. Santos, and A.L. Braga Tetrahedron Lett. 43 2002 7517 7520
64. J. Gerard, and L. Hevesi Tetrahedron 57 2001 9109 9122
65. C.-Q. Zhao, and X. Huang Synth. Commun. 26 1996 3607 3612
66. M. Tingoli, M. Tiecco, L. Testaferri, A. Temperini, G. Pelizzi, and A. Bacchi Tetrahedron 51 1995 4691 4700
67. M. Terada, S. Matsukawa, and K. Mikami Chem. Commun. 1993 327 328
68. M. Tingoli, M. Tiecco, L. Testaferri, and D. Chianelli Gazz. Chim. Ital. 121 1991 59 61
69. T.G. Back, S. Collins, M.V. Krishna, and K.W. Law J. Org. Chem. 52 1987 4258 4264