Borylated Tetrazoles from Cycloaddition of Azide Anions to Nitrilium Derivatives of closo-Decaborate Clusters
Publication type: Journal Article
Publication date: 2013-10-10
scimago Q2
wos Q1
SJR: 0.676
CiteScore: 5.1
Impact factor: 2.9
ISSN: 02767333, 15206041
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
Interaction of the closo-decaborate clusters [Bun4N][B10H9(NCR)] (R = Me 1a, Et 1b, But 1c, Ph 1d) with the azide [Ph3PNPPh3]N3 proceeds immediately upon mixing the reagents in an MeCN solution at RT, giving the borylated 1,5-disubstituted tetrazoles [B10H9(N4CR)]2– in essentially quantitative yield. On a synthetic scale, sodium azide, NaN3, reacts similarly with the nitrile functionality of 1a–d in an acetonitrile suspension under mild conditions (RT, 15 h) to afford selectively the borylated tetrazoles [Bun4N]2[B10H9(N4CR)] (2a–d; 88–96% isolated yields) and the water-soluble Na2[B10H9(N4CR)] species (3a–d; ca. 95% isolated yield) after the metathetical reaction with NaBPh4 in MeOH/H2O. The reaction with N3– represents the first example of the propargyl-allenyl anion type dipole cycloaddition (CA) to the nitrilium derivatives of any boron clusters. Reactions of 1a–d with alkyl or aryl azides (p-Me-C6H4-COCH2N3, p-NO2-C6H4-CH2N3, PhN3) do not proceed even under harsh conditions (2 d, dry EtCN, 100 °C, un...
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Total citations:
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Citations from 2024:
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Mindich A. L. et al. Borylated Tetrazoles from Cycloaddition of Azide Anions to Nitrilium Derivatives of closo-Decaborate Clusters // Organometallics. 2013. Vol. 32. No. 21. pp. 6576-6586.
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Mindich A. L., Bokach N. A., Kuznetsov M., Starova G. L., Zhdanov A. P., Novikov A. S., Miltsov S. A., Grigoriev M. S., Kukushkin V. Y. Borylated Tetrazoles from Cycloaddition of Azide Anions to Nitrilium Derivatives of closo-Decaborate Clusters // Organometallics. 2013. Vol. 32. No. 21. pp. 6576-6586.
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RIS
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TY - JOUR
DO - 10.1021/om400892x
UR - https://doi.org/10.1021/om400892x
TI - Borylated Tetrazoles from Cycloaddition of Azide Anions to Nitrilium Derivatives of closo-Decaborate Clusters
T2 - Organometallics
AU - Mindich, Aleksey L.
AU - Bokach, Nadezhda A.
AU - Kuznetsov, Maxim
AU - Starova, G. L.
AU - Zhdanov, Andrey P.
AU - Novikov, Alexander S.
AU - Miltsov, Serguei A
AU - Grigoriev, Mikhail S.
AU - Kukushkin, Vadim Yu.
PY - 2013
DA - 2013/10/10
PB - American Chemical Society (ACS)
SP - 6576-6586
IS - 21
VL - 32
SN - 0276-7333
SN - 1520-6041
ER -
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BibTex (up to 50 authors)
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@article{2013_Mindich,
author = {Aleksey L. Mindich and Nadezhda A. Bokach and Maxim Kuznetsov and G. L. Starova and Andrey P. Zhdanov and Alexander S. Novikov and Serguei A Miltsov and Mikhail S. Grigoriev and Vadim Yu. Kukushkin},
title = {Borylated Tetrazoles from Cycloaddition of Azide Anions to Nitrilium Derivatives of closo-Decaborate Clusters},
journal = {Organometallics},
year = {2013},
volume = {32},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/om400892x},
number = {21},
pages = {6576--6586},
doi = {10.1021/om400892x}
}
Cite this
MLA
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Mindich, Aleksey L., et al. “Borylated Tetrazoles from Cycloaddition of Azide Anions to Nitrilium Derivatives of closo-Decaborate Clusters.” Organometallics, vol. 32, no. 21, Oct. 2013, pp. 6576-6586. https://doi.org/10.1021/om400892x.