Preparation of benzocyclobutenone derivatives based on an efficient generation of benzynes (Bicyclo[4.2.0]octa-1,3,5-trien-7-one, 5-(phenylmethoxy)-)

Organic Syntheses

Volumn 84, Issue , 2007, Pages 272-284

  Tsujiyama, Shin ichiro ^c   Suzuki, Keisuke ^a   Guthrie, David B ^c   Gibney, Heather M ^c   Curran, Dennis P ^b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b UNIVERSITY OF PITTSBURGH   (United States)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85026886511     PISSN: 00786209     EISSN: 16000730     Source Type: Book Series    
DOI: 10.15227/orgsyn.084.0272     Document Type: Article

References (24)

1. For reviews on benzocyclobutenes, see: (a) Wada, Y.; Tago, T.; Nishimura, J. J. Synth. Org. Chem. Jpn. 1992, 50, 616;
2. (b) Farona, M. F. Prog. Polym. Sci. 1996, 21, 505;
3. (c) Michellys, P.-Y.; Pellissier, H.; Santelli, M. Org. Prep. Proced. Int. 1996, 28, 545;
4. (d) Segura, J. L.; Martín, N. Chem. Rev. 1999, 99, 3199;
5. (e) Mehta, G.; Kotha, S. Tetrahedron 2001, 57, 625;
6. (f) Sadana, A. K.; Saini, R. K.; Billups, W. E. Chem. Rev. 2003, 103, 1539.
7. (a) Hosoya, T.; Hasegawa, T.; Kuriyama, Y.; Matsumoto, T.; Suzuki, K. Synlett 1995, 177;
8. (b) Hamura, T.; Hosoya, T.; Yamaguchi, H.; Kuriyama, Y.; Tanabe, M.; Miyamoto, M.; Yasui, Y.; Matsumoto, T.; Suzuki, K. Helv. Chim. Acta 2002, 85, 3589.
9. (a) Matsumoto, T.; Hosoya, T.; Suzuki, K. J. Am. Chem. Soc. 1992, 114, 3568;
10. (b) Hosoya, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1994, 116, 1004.
11. (a) Ohmori, K.; Kitamura, M.; Suzuki, K. Angew. Chem. Int. Ed. 1999, 38, 1226;
12. (b) Kitamura, M.; Ohmori, K.; Kawase, T.; Suzuki, K. Angew. Chem. Int. Ed. 1999, 38, 1229.
13. (a) Matsumoto, T.; Yamaguchi, H.; Hamura, T.; Tanabe, M.; Kuriyama, Y.; Suzuki, K. Tetrahedron Lett. 2000, 41, 8383;
14. (b) Yamaguchi, H.; Konegawa, T.; Tanabe, M.; Nakamura, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 2000, 41, 8389;
15. (c) Matsumoto, T.; Yamaguchi, H.; Tanabe, M.; Yasui, Y.; Suzuki, K. Tetrahedron Lett. 2000, 41, 8393.
16. Ohmori, K.; Mori, K.; Ishikawa, Y.; Tsuruta, H.; Kuwahara, S.; Harada, N.; Suzuki, K. Angew. Chem. Int. Ed. 2004, 43, 3167.
17. Kessar, S. V. In Comprehensive Organic Synthesis; Trost, B. M. Ed., Pergamon: Oxford, U. K., 1991, Vol. 4, pp 483–515;
18. (b) Pellissier, H.; Santelli, M. Tetrahedron 2003, 59, 701.
19. Friedman, L.; Logullo, F. M. J. Am. Chem. Soc. 1963, 85, 1549.
20. Wittig, G. Org. Synth. 1959, 39, 75 (Coll. Vol. 4, 1963, 964)
21. Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211.
22. Matsumoto, T.; Hosoya, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1991, 32, 6735.
23. The mono-cleavage process is analogous to mono-saponification of bis-benzoate: Zaugg, H. E. J. Org. Chem. 1976, 41, 3419.
24. Matsumoto, T.; Sohma, T.; Hatazaki, S.; Suzuki, K. Synlett 1993, 843.