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Issue 1, 2010
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Low and high temperature bromination of 2,3-dicarbomethoxy and 2,3-dicyano benzobarrelene: unexpected substituent effect on bromination

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Abstract

The bromination of 2,3-dicarbomethoxy benzobarrelene yielded the dibromide regio- and stereospecifically arising from the aryl shift where the bromine exclusively attacks the double bond from the exo face of the double bond. High temperature bromination of this compound yielded aryl-shift products. From the low temperature bromination of 2,3-dicyano benzobarrelene, non-rearranged products were obtained along with the rearranged products. Surprisingly, we observed that the yield of non-rearranged products decreased on increasing the temperature. A possible role of the substituent was discussed using DFT calculations on model compounds.

Graphical abstract: Low and high temperature bromination of 2,3-dicarbomethoxy and 2,3-dicyano benzobarrelene: unexpected substituent effect on bromination

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Publication details

The article was received on 28 Jul 2009, accepted on 29 Sep 2009 and first published on 02 Nov 2009


Article type: Paper
DOI: 10.1039/B9NJ00372J
Citation: New J. Chem., 2010,34, 141-150

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    Low and high temperature bromination of 2,3-dicarbomethoxy and 2,3-dicyano benzobarrelene: unexpected substituent effect on bromination

    S. Taşkesenlioğlu, A. Daştan, E. Dalkılıç, M. Güney and R. Abbasoğlu, New J. Chem., 2010, 34, 141
    DOI: 10.1039/B9NJ00372J

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