High Temperature Bromination of Benzobicyclo[2.2.2]Octa-2,5-Diene Derivatives: Alternative Synthesis of Di-, Tri- and Tetra-Bromobenzobarrelenes

Daştan, Arif

doi:10.3184/030823406776330963

Journal of Chemical Research

2006

DOI: 10.3184/030823406776330963

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High Temperature Bromination of Benzobicyclo[2.2.2]Octa-2,5-Diene Derivatives: Alternative Synthesis of Di-, Tri- and Tetra-Bromobenzobarrelenes

Arif Daştan

Abstract: The electrophilic bromination of benzobarrelene derivatives has been studied and alternative synthetic methods developed for, di-, tri-and tetrabromobenzobarrelenes.

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Cited by 2 publications

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Norbornanoid Chiral Ketones by Desymmetrization of Dibromoalkenes

Koçak

Borsato

Lucchi

et al. 2014

Helvetica Chimica Acta

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New optically active polycyclic ketones 6a-6d, amenable to a large variety of synthetic applications, have been prepared from readily available 2,3-dibromonorbornene and analogs (Scheme 2) via desymmetrization with (-)-ephedrine, followed by hydrolysis under mild acidic conditions. At variance with substrates 4a-4d, the sterically hindered norbornene derivative 4e reacts with the solvent N-methylpyrrolidin-2-one (NMP) leading to the formation of the unusual cyclopropanoid products 8a and 8b

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Norbornanoid Chiral Ketones by Desymmetrization of Dibromoalkenes

Koçak

Borsato

Lucchi

et al. 2014

Helvetica Chimica Acta

View full text Add to dashboard Cite

show abstract

The first and efficient synthesis of some of the polyhalogenated benzobarrelenes: unusual formation of a benzosemibullvalene derivative

Şengül¹,

Gültekin²,

Eşsiz³

et al. 2009

Tetrahedron

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High Temperature Bromination of Benzobicyclo[2.2.2]Octa-2,5-Diene Derivatives: Alternative Synthesis of Di-, Tri- and Tetra-Bromobenzobarrelenes

Abstract: The electrophilic bromination of benzobarrelene derivatives has been studied and alternative synthetic methods developed for, di-, tri-and tetrabromobenzobarrelenes.

Cited by 2 publications

References 32 publications

Norbornanoid Chiral Ketones by Desymmetrization of Dibromoalkenes

Norbornanoid Chiral Ketones by Desymmetrization of Dibromoalkenes

The first and efficient synthesis of some of the polyhalogenated benzobarrelenes: unusual formation of a benzosemibullvalene derivative

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