Nickel-mediated cyclobutabenzene syntheses. trans-7,8-dibromo-cyclobutabenzenes: 1 Their one-pot preparation, x-ray structure, and Diels-Alder reactions

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2549-2552

  Stanger, Amnon ^a   Ashkenazi, Nissan ^a   Shachter, Alona ^a   Bläser, Dieter ^b   Stellberg, Peter ^b   Boese, Roland ^b  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^b UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001487534     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9516852     Document Type: Article

References (38)

1. Alternative name: trans-1,2-dibromobenzocyclobutene.
2. (a) Technion. (b) Essen.
3. Alternative name. o-quinodimethanes.
4. Oppolzer, W. Synthesis 1978, 793.
5. (a) Boese, R.; Bläser, D Angew. Chem., Int. Ed. Engl. 1988, 27, 304.
6. (b) Boese, R.; Bläser, D.; Billups, W. E.; Haley, M. M.; Maulitz, A. H.; Mohler, D. L.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1994, 33, 313.
7. (c) Stanger, A. J. Am. Chem. Soc. 1991, 113, 8277 and references therein.
8. (d) Siegel, J. S. Angew. Chem., Int. Ed. Engl. 1994, 33, 1721.
9. Cava, M. P.; Napier, D. R. J. Am. Chem. Soc. 1956, 78, 500
10. In a control experiment using Cava's procedure we obtained trans- and cis-dibromo and diiodocyclobutabenzene in a ratio of 63: 19:12:6, respectively. The yield of pure 3 obtained from this procedure (mp = 52.4-52.8°C) after repeated recrystallization is 4.8%. See: Cava, M. P.; Napier, D. R. J. Am. Chem. Soc. 1957, 79, 1701.
11. (a) Sanders, A.; Giering, W. P. J. Org. Chem. 1973, 38, 3055.
12. (b) Cava, M. P., Napier, D. R. J. Am. Chem. Soc. 1958, 80, 2255.
13. Cava, M. P.; Deana, A. A.; Muth, K. J. Am. Chem. Soc. 1959, 81, 6458.
14. Funk, R. L.; Vollhardt, K. P C. J. Am. Chem Soc. 1976, 98, 6755.
15. Another drawback is the necessity to prepare the diyne that is not commercially available.
16. (a) Semmelhack, M. F.; Helquist, P. M.; Jones, D. J. Am. Chem. Soc. 1971, 93, 5908.
17. (b) Semmelhack, M. F.; Ryono, L. S. J. Am. Chem. Soc. 1975, 97, 3873.
18. (c) Kende, A. S.; Liebeoking, L. S.; Braitsch, D. M. Tetrahedron Lett. 1975, 3375.
19. (d) Zembayashi, M.; Tameo, K.; Yoshida, J.; Kumada, M. Tetrahedron Lett. 1977, 4089.
20. (e) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 7549.
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22. Stanger, A.; Shazar, A. J. Organomet. Chem. 1993, 458, 233.
23. n
24. 2NiL (L = COD, anthracene), but only starting materials were isolated. Thus, no coupling is observed when a bidentate ligand is used, and a bisphosphine leads only to dimerization.
25. 2NiL (L = COD, anthracene), but only starting materials were isolated. Thus, no coupling is observed when a bidentate ligand is used, and a bisphosphine leads only to dimerization.
26. 2NiL (L = COD, anthracene), but only starting materials were isolated. Thus, no coupling is observed when a bidentate ligand is used, and a bisphosphine leads only to dimerization.
27. Yamamoto, T.; Wakabayashi, S.; Osakada, K. J. J. Organomet. Chem. 1992, 428, 223.
28. 1H NMR: 3, 7.39, 7.19 (AA′BB′, 4H), 5.41 (s, 2H, CHBr); 4, 7.43, 7.26 (AA′BB′, 4H), 5.81 (s, 2H, CHBr). See Fraenkel, G.; Asahi, Y.; Mitchell, M. J.; Cava, M. P. Tetrahedron 1964, 20, 1179.
29. Mp 52.7-52-8°C (uncorrected) and GC analysis of the crystals show that they contain 99.7% 3 and 0.3% 4.
30. No starting material, however, was recovered, and most products were Wurtz type.
31. -3. Further details are given in Table 1
32. (a) Mueller, P.; Rey, M. Helv. Chim. Acta 1981, 64, 354.
33. (b) Ito, Y.; Nakatsuka, M.; Saegusa, T. J. Am. Chem. Soc. 1982, 104, 7609.
34. Stanger, A: Ashkenazi, N.; Blaser, D.; Stellberg, P.; Mauliz, A.; Boese. R. manuscript in preparation.
35. Cava, M. P.; Van Meter, J. P. J. Org. Chem. 1969, 34, 538.
36. 6.
37. (a) Guyot, M.; Mentzer, C. Bull. Soc. Chem. Fr. 1967, 1843.
38. (b) Wenkert, E.; Michelotti, E. L.; Swindel, C. S.; Tingoli, M. J. Org. Chem. 1984, 49, 4894.