Nucleophilic addition reactions to nitrilium derivatives [B12H11NCCH3]− and [B12H11NCCH2CH3]−. Synthesis and structures of closo-dodecaborate-based iminols, amides and amidines

Julia Laskova; Ivan Ananiev; Irina Kosenko; Alexander Serdyukov; Marina Stogniy; Igor Sivaev; Mikhail Grin; Andrey Semioshkin; Vladimir I. Bregadze

doi:10.1039/D1DT04174F

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Nucleophilic addition reactions to nitrilium derivatives [B₁₂H₁₁NCCH₃]⁻ and [B₁₂H₁₁NCCH₂CH₃]⁻. Synthesis and structures of closo-dodecaborate-based iminols, amides and amidines†‡

Julia Laskova,

*^a Ivan Ananiev,

^ab Irina Kosenko,^a Alexander Serdyukov,

^ac Marina Stogniy,

^ac Igor Sivaev,

^a Mikhail Grin,^c Andrey Semioshkin^a and Vladimir I. Bregadze^a

Author affiliations

* Corresponding authors

^a A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., Moscow, Russia
E-mail: Laskova@ineos.ac.ru

^b G.V. Plekhanov Russian University of Economics, 117997, 36, Stremyanny line, Moscow, Russia

^c M. V. Lomonosov Institute of Fine Chemical Technology, MIREA – Russian Technological University, 86 Vernadsky Av., Moscow, Russia

Abstract

The synthesis of the acetonitrilium and propionitrilium derivatives of closo-dodecaborate [B₁₂H₁₂]²⁻ was discussed. The nucleophilic addition reactions of water, alcohols and secondary amines to the activated triple bond of the nitrilium derivatives yielded the corresponding iminols, imidates and amidines. The obtained results were supported by X-ray diffraction studies and DFT calculations.

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DOI: https://doi.org/10.1039/D1DT04174F
Article type: Communication
Submitted: 12 Dec 2021
Accepted: 17 Jan 2022
First published: 18 Jan 2022

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Dalton Trans., 2022,51, 3051-3059

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Nucleophilic addition reactions to nitrilium derivatives [B₁₂H₁₁NCCH₃]⁻ and [B₁₂H₁₁NCCH₂CH₃]⁻. Synthesis and structures of closo-dodecaborate-based iminols, amides and amidines

J. Laskova, I. Ananiev, I. Kosenko, A. Serdyukov, M. Stogniy, I. Sivaev, M. Grin, A. Semioshkin and V. I. Bregadze, Dalton Trans., 2022, 51, 3051 DOI: 10.1039/D1DT04174F

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Dalton Transactions