High temperature bromination Part XXIII: Bromination of octahydro-1H-indene and octahydro-1H-4,7-methanoindene

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2013-12-11

Author

Özer, Melek Sermin
Kilbas, Benan
Balcı, Metin

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Thermal and photobromination of octahydro-1H-indene and octahydro-1H-4,7-methanoindene were investigated. Three isomeric tetrabromides (1,3,4,7-tetrabromo-2,3,4,5,6,7-hexahydro-1-H-indene) were formed along with a smaller amount of tribromoindane and a pentabromide by thermal bromination of octahydro-1H-indene. The thermodynamically most stable isomers were formed. Morover, thermal and photochemical bromination of octahydro-1H-4,7-methanoindene furnished bromides resulting regiospecifically from the allylic bromination of the five-membered ring. Furthermore, the double bond formed as the intermediate functional group was also brominated due to its pyramidalization. The mechanism proposed for the formation of product distribution was discussed.

Subject Keywords

Organic Chemistry, Bromination, High temperature bromination, Hydrocarbons, Substitution

URI

https://hdl.handle.net/11511/51197

Journal

Arkivoc

DOI

https://doi.org/10.3998/ark.5550190.p008.195

Collections

Department of Chemistry, Article

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Citation Formats

M. S. Özer, B. Kilbas, and M. Balcı, “High temperature bromination Part XXIII: Bromination of octahydro-1H-indene and octahydro-1H-4,7-methanoindene,” Arkivoc, 2013, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/51197.