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Issue 32, 2018
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Formation of borata-alkene/iminium zwitterions by ynamine hydroboration

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Abstract

The ynamine TMP–C[triple bond, length as m-dash]C–CH3 adds HB(C6F5)2 to give the unsaturated C2-bridged N/B FLP 5. Compound 5 shows the structural data indicating a marked participation of the zwitterionic mesomeric borata-alkene/iminium form. It splits dihydrogen at r.t. with Z- to E-isomerization at the central C[double bond, length as m-dash]C double bond. Hydroboration of the ynamine Me3Si–C[triple bond, length as m-dash]C–NiPr2 with HB(C6F5)2 yields a N/B FLP that shows a strongly distorted central C[double bond, length as m-dash]C double bond with a rotation of the planes of the substituent pairs at its ends by ca. 57°.

Graphical abstract: Formation of borata-alkene/iminium zwitterions by ynamine hydroboration

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Publication details

The article was received on 13 Jun 2018, accepted on 20 Jun 2018 and first published on 23 Jun 2018


Article type: Communication
DOI: 10.1039/C8DT02435A
Citation: Dalton Trans., 2018,47, 10853-10856
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    Formation of borata-alkene/iminium zwitterions by ynamine hydroboration

    L. Wang, Z. Jian, C. G. Daniliuc, G. Kehr and G. Erker, Dalton Trans., 2018, 47, 10853
    DOI: 10.1039/C8DT02435A

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