Impressive changeover of reaction course in ring expansion of styrylbenzocyclobutenol under alkoxide-forming conditions

Tetrahedron Letters

Volumn 47, Issue 37, 2006, Pages 6677-6679

  Takemura, Isao ^a   Matsumoto, Takashi ^a   Suzuki, Keisuke ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL COMPOUND; NAPHTHALENE; STYRYLBENZOCYCLOBUTENOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS; THERMAL STIMULATION;

EID: 33746834891     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.079     Document Type: Article

References (9)

1. Takemura, I.; Imura, K.; Matsumoto, T.; Suzuki, K., see preceding paper. Tetrahedron Lett. 2006, 47, doi:10.1016/j.tetlet.2006.06.078.
2. *.{A figure is presented}
3. Conversion to the corresponding quinone derivative 10 was the additional structure proof.{A figure is presented}
4. Crystallographic data (excluding structure factors) for the structures in this letter have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 243852 (for compound 5) and 244793 (for compound 10). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1 EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk].
5. Since considerable data have been accumulated for the role of homolytic processes in the related system, the corresponding radical-based mechanism also could be possible, including homolysis of the four-membered ring to form a diradical 11 followed by recombination via 12.{A figure is presented}.
6. Roth W.R., Rekowski V., Börner S., and Quast M. Liebigs Ann. Chem. (1996) 409-430
7. Paul T., Boese R., Steller I., Bandmann H., Gescheidt G., Korth H.-G., and Sustmann R. Eur. J. Org. Chem. (1999) 551-563
8. Gibson D.H., and DePuy C.H. Chem. Rev. 74 (1974) 605-624
9. Compound 13 was also obtained in 10% yield as a side product.{A figure is presented}