Linkage Isomerism Leading to Contrasting Carboboration Chemistry: Access to Three Constitutional Isomers of a Borylated Phosphaalkene |
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| Authors: | Dr. Daniel W. N. Wilson Dr. Meera Mehta Mauricio P. Franco Prof. Dr. John E. McGrady Prof. Dr. Jose M. Goicoechea |
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| Affiliation: | 1. Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA UK;2. Department of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL UK;3. Instituto de Química, University of São Paulo, Av. Prof. Lineu Prestes, 748—Vila Universitaria, São Paulo—SP, 05508-000 Brazil |
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| Abstract: | We describe the reactivity of two linkage isomers of a boryl-phosphaethynolate, [B]OCP and [B]PCO (where [B]=N,N’-bis(2,6-diisopropylphenyl)-2,3-dihydro-1H-1,3,2-diazaboryl), towards tris- (pentafluorophenyl)borane (BCF). These reactions afforded three constitutional isomers all of which contain a phosphaalkene core. [B]OCP reacts with BCF through a 1,2 carboboration reaction to afford a novel phosphaalkene, E-[B]O{(C6F5)2B}C=P(C6F5), which subsequently undergoes a rearrangement process involving migration of both the boryloxy and pentafluorophenyl substituents to afford Z-{(C6F5)2B}(C6F5)C=PO[B]. By contrast, [B]PCO undergoes a 1,3-carboboration process accompanied by migration of the N,N’-bis(2,6-diisopropylphenyl)-2,3-dihydro-1H-1,3,2-diazaboryl to the carbon centre. |
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| Keywords: | boryl groups carboboration isomerism phosphaalkenes phosphaethynolates |
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