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Issue 22, 2018
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Nucleophilic addition reactions to the ethylnitrilium derivative of nido-carborane 10-EtC[triple bond, length as m-dash]N-7,8-C2B9H11

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Abstract

Alkylnitrilium derivatives of nido-carborane 10-RC[triple bond, length as m-dash]N-7,8-C2B9H11 (R = Me, Et) have been prepared by the reaction of the parent anion [7,8-C2B9H12] with mercury(II) chloride in mixtures of the corresponding nitriles and benzene. Hydrolysis of 10-EtC[triple bond, length as m-dash]N-7,8-C2B9H11 resulted in iminol 10-EtC(OH)[double bond, length as m-dash]HN-7,8-C2B9H11 which on treatment with a base gave the corresponding amide 10-EtC([double bond, length as m-dash]O)HN-7,8-C2B9H11. The reactions of 10-EtC[triple bond, length as m-dash]N-7,8-C2B9H11 with alcohols and thiols were found to give stable imidates and thioimidates 10-EtC(XR)[double bond, length as m-dash]HN-7,8-C2B9H11 (X = O, R = Me, Et, iPr, Bu; X = S, R = Et, Bu, Hx) as mixtures of E- and Z-isomers that were successfully separated by column chromatography. The crystal molecular structures of E-10-EtC(OR)[double bond, length as m-dash]HN-7,8-C2B9H11 (R = Et, i-Pr, Bu) and Z-10-EtC(SEt)[double bond, length as m-dash]HN-7,8-C2B9H11 were determined by single crystal X-ray diffraction.

Graphical abstract: Nucleophilic addition reactions to the ethylnitrilium derivative of nido-carborane 10-EtC [[triple bond, length as m-dash]] N-7,8-C2B9H11

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Publication details

The article was received on 16 Aug 2018, accepted on 26 Sep 2018 and first published on 27 Sep 2018


Article type: Paper
DOI: 10.1039/C8NJ04192J
Citation: New J. Chem., 2018,42, 17958-17967
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    Nucleophilic addition reactions to the ethylnitrilium derivative of nido-carborane 10-EtC[triple bond, length as m-dash]N-7,8-C2B9H11

    M. Yu. Stogniy, S. A. Erokhina, K. Yu. Suponitsky, A. A. Anisimov, I. B. Sivaev and V. I. Bregadze, New J. Chem., 2018, 42, 17958
    DOI: 10.1039/C8NJ04192J

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