Bromination of 'endo-benzocyclobutanorbornene': Synthesis of 'endo-11,12-dibromobenzocyclobutanorbornene': High-temperature bromination - Part XIV

Date

2002-01-01

Author

Dastan, A
Uzundumlu, E
Balcı, Metin

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The electrophilic addition of Br to 'endo-benzocyclobutanorbornene' 5 at -50degrees led in high yield to the formation of the rearranged dibromides 6 and 7. However, high-temperature bromination of 5 in decalin at 150degrees gave exclusively nonrearranged product 8 in 98% yield. From the elimination of nonrearranged product 8, 'endo-bromobenzocyclobutanorbornene' 9 and 'endo-benzocyclobutanorbornene' 5 were obtained. Similarly. bromination of monobromide 9 at 77degrees yielded the nonrearranged tribromide 12 in quantitative yield. The dehydrobromination of 12 provided the 'endo 11,12-dibromobenzocyclobutanorbornene' 3 in high yield, which is a synthon for the trimerization reactions.

Subject Keywords

Cyclotrimerization, 2,3-Dibromobenzobarrelene, Derivatives

URI

https://hdl.handle.net/11511/56404

Journal

HELVETICA CHIMICA ACTA

DOI

https://doi.org/10.1002/1522-2675(200209)85:9<2729::aid-hlca2729>3.0.co;2-#

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

A. Dastan, E. Uzundumlu, and M. Balcı, “Bromination of ‘endo-benzocyclobutanorbornene’: Synthesis of ‘endo-11,12-dibromobenzocyclobutanorbornene’: High-temperature bromination - Part XIV,” HELVETICA CHIMICA ACTA, pp. 2729–2739, 2002, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56404.