Controlled synthesis of substituted benzobasketene derivatives

Date

2003-01-01

Author

Aydinli, B
Celik, M
Gultekin, MS
Uzun, O
Balcı, Metin

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The addition of benzyne to trans-7,8-dibromobicyclo[4.2.0]octa-2,4-diene (6) led to the formation of dibromide 7. The dehydrobromination of 7 followed by replacement of the Br-atom with a CN substituent gave 9. Photolysis of 9 in acetone at 254 nm yielded the desired monosubstituted benzobasketene derivative 10. Bromination of monobromide 8 followed by dehydrobromination furnished the symmetrically substituted dibromo compound 15. Further bromination of 7 followed by dehydrobromination resulted in the formation of the dibromides 20 and 21. Substitution of the Br-atoms in 15, 20, and 21 with CN substituents and photolysis of the formed dicarbonitriles 16, 23, and 24 gave the target benzobasketene-dicarbonitriles 17, 25, and 26, respectively.

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis

URI

https://hdl.handle.net/11511/56422

Journal

HELVETICA CHIMICA ACTA

DOI

https://doi.org/10.1002/hlca.200390276

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

B. Aydinli, M. Celik, M. Gultekin, O. Uzun, and M. Balcı, “Controlled synthesis of substituted benzobasketene derivatives,” HELVETICA CHIMICA ACTA, pp. 3332–3341, 2003, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56422.