Generation and intramolecular cyclization of (2- ethenylphenyl)bisketenes. Synthesis of benzofuranones

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3643-3646

  Heileman, Matthew J ^a   Moore, Harold W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; FURANONE DERIVATIVE; KETENE DERIVATIVE; NAPHTHOFURANONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

EID: 0032575154     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00638-8     Document Type: Article

References (15)

1. 1. Turnbull, P.; Heileman, M. J.; Moore, H. W. J. Org. Chem. 1996, 61, 2584.
2. 2. For a recent review on the ring expansion of cyclobutenones see: Moore, H. W.; Yerxa B. R. Adv. Strain Org. Chem. 1995, 4, 81-162.
3. 3. For analogies for these 1,7-shifts see: (a) Marvell, E. N.; Caple, G.; Schatz, B.; and Pippin, W. Tetrahedron 1973, 29, 3781-3789.
4. (b) Marvell, E. N.; Caple, G.; Delphey, C.; Platt, J.; Polston, N.; and Tashiro, J. Tetrahedron 1973, 29, 3806.
5. (c) Baldwin, J. E.; and Reddy, V. P. J. Org. Chem. 1988, 53, 1129.
6. 4. The structure assignments of the new compounds reported here are in strict agreement with their spectral and analytical data.
7. 5. Gayo, L.; Moore, H. W. J. Org. Chem. 1992, 57, 6896.
8. 6. 2-Lithio-1-ethenylbenzene was prepared by treating 2-bromostyrene with n-butyllithium.
9. 7. Another route to differentially substituted cyclobutenediones exists, but was ineffective when both subtituents were unsaturated. Liebeskind, L. S. ; Fengl, R. W.; Wirtz, K. R.; and Shawe, T. T. J. Org. Chem. 1988, 53, 2482.
10. 8. For an excellent discussion of ketenes including bisketenes see (a) Tidwell, T. T. Ketenes; Wiley: New York, NY, 1995;
11. (b) Alien, A. D.; Ronghua, L.; Ma, Jihai, McAllister, M. A., Tidwell, T. T.; and Zhao, Da. Pure & Appl. Chem. 1995, 67, 777-782;
12. (c) Egle, I.; Lai, W.-Y.; Moore, P. A.; Renton, P.; Tidwell, T. T.; and Zhao, D. J. Org. Chem. 1997, 62, 18-25.
13. 9. (a) Anacardio, R.; Arcadi, A.; D'Anniballe, G.; Marinelli, F. Synthesis 1995, 831 and references therein.
14. (b) Ramachandran, P.V.; Chen, G.-M.; Brown, H. C. Tetrahedron Lett. 1996, 37, 2205 and references therein.
15. (c) Satoh, T.; Tsuda, T.; Kushino, Y.; Miura, M.; and Masakatsu, N. J. Org. Chem. 1996, 61, 6476-6477.