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2017•Philosophical Transactions of the Royal Society A Mathematical Physical and Engineering SciencesOpen access

Design and reactions of a carbon Lewis base/boron Lewis acid frustrated Lewis pair

Jennifer Möricke, Birgit Wibbeling, Constantin Gabriel Daniliuc, Gerald Kehr, Gerhard Erker

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Abstract

The conjugated dienamine 4 selectively adds Piers' borane [HB(C 6 F 5 ) 2 ] to give the enamine/borane system 5 , which features a boratirane structure by internal enamine carbon Lewis base to boron Lewis acid interaction. Compound 5 behaves as a C/B frustrated Lewis pair and undergoes typical addition reactions to benzaldehyde, several nitriles and to sulfur dioxide. This article is part of the themed issue ‘Frustrated Lewis pair chemistry’.

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The conjugated dienamine 4 selectively adds Piers' borane [HB(C 6 F 5 ) 2 ] to give the enamine/borane system 5 , which features a boratirane structure by internal enamine carbon Lewis base to boron Lewis acid interaction. Compound 5 behaves as a C/B frustrated Lewis pair and undergoes typical addition reactions to benzaldehyde, several nitriles and to sulfur dioxide. This article is part of the themed issue ‘Frustrated Lewis pair chemistry’.

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Available abstract

The conjugated dienamine 4 selectively adds Piers' borane [HB(C 6 F 5 ) 2 ] to give the enamine/borane system 5 , which features a boratirane structure by internal enamine carbon Lewis base to boron Lewis acid interaction. Compound 5 behaves as a C/B frustrated Lewis pair and undergoes typical addition reactions to benzaldehyde, several nitriles and to sulfur dioxide. This article is part of the themed issue ‘Frustrated Lewis pair chemistry’.

Key concepts: Frustrated Lewis pair, Lewis acids and bases, Borane, Enamine, Electron pair, Chemistry, Boron, Polymer chemistry

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