The effect of the double bond pyramidalization on the mode of the bromination reaction: Bromination of benzobicyclononadiene

Date

2007-06-22

Author

Balcı, Metin
Guney, Murat
Dastan, Arif
Azizoglu, Akin

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The bromination of 6,7,8,9-tetrahydro-5H-5,9-ethenobenzo[a][7]annulene yielded regio- and stereospecifically formed dibromides arising from the alkyl shift where the bromine exclusively attacks the double bond from the endo face of the double bond. DFT calculations on model compounds showed that the pyramidalization of the double bond and steric repulsion caused by the methylene protons are responsible for the stereo- and regioselective addition of bromine.

Subject Keywords

Organic Chemistry

URI

https://hdl.handle.net/11511/57862

Journal

JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1021/jo070253b

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

M. Balcı, M. Guney, A. Dastan, and A. Azizoglu, “The effect of the double bond pyramidalization on the mode of the bromination reaction: Bromination of benzobicyclononadiene,” JOURNAL OF ORGANIC CHEMISTRY, pp. 4756–4762, 2007, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57862.