High temperature bromination. Part 22: Bromination of 1a,2,7,7a-tetrahydro-1H-cyclopropa[b] naphthalene

Date

2007-08-20

Author

Demirci-Gueltekin, Demet
Guenbas, Duygu D.
TAŞKESENLİGİL, Yavuz
Balcı, Metin

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The high-temperature bromination of 1a,2,7,7a-tetrahydro-1H-cyclopropa[b] naphthalene and its carboethoxy derivative was studied. Reaction of the title compound with 1 mol of bromine in refluxing carbon tetrachloride resulted in the formation of ring-opening products. In the case of the carboethoxy derivative,bromination took place both regio- and stereospecifically at the benzylic positions,the cyclopropane ring did not undergo bond cleavage. A mechanism for the formation of the products and their dehydrobromination reactions is discussed.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/51824

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2007.05.124

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

D. Demirci-Gueltekin, D. D. Guenbas, Y. TAŞKESENLİGİL, and M. Balcı, “High temperature bromination. Part 22: Bromination of 1a,2,7,7a-tetrahydro-1H-cyclopropa[b] naphthalene,” TETRAHEDRON, pp. 8151–8156, 2007, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/51824.