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Issue 31, 2019
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Synthetic, structural and reaction chemistry of N-heterocyclic germylene and stannylene compounds featuring N-boryl substituents

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Abstract

This study details the syntheses of N-heterocyclic germylenes and stannylenes featuring diazaborolyl groups, {(HCDippN)2B} (Dipp = 2,6-iPr2C6H3), as both of the N-bound substituents, with a view to generating electron rich and sterically protected metal centres. The energies of their key frontier orbitals – the group 14-centred lone pair and orthogonal pπ-orbital (typically the HOMO−2 and LUMO) have been probed by DFT calculations and compared with a related acyclic analogue, revealing (in the case of the stannylenes) a correlation with the measured 119Sn chemical shifts. The reactivity of the germylene systems towards oxygen atom transfer agents has been examined, with 2 : 1 reaction stoichiometries being observed for both Me3NO and pyridine N-oxide, leading to the formation of products thought to be derived from the activation of C–H bonds by a transient first-formed germanone.

Graphical abstract: Synthetic, structural and reaction chemistry of N-heterocyclic germylene and stannylene compounds featuring N-boryl substituents

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Article information


Submitted
09 Jun 2019
Accepted
10 Jul 2019
First published
10 Jul 2019

Dalton Trans., 2019,48, 11951-11960
Article type
Paper

Synthetic, structural and reaction chemistry of N-heterocyclic germylene and stannylene compounds featuring N-boryl substituents

L. Kristinsdóttir, N. L. Oldroyd, R. Grabiner, A. W. Knights, A. Heilmann, A. V. Protchenko, H. Niu, E. L. Kolychev, J. Campos, J. Hicks, K. E. Christensen and S. Aldridge, Dalton Trans., 2019, 48, 11951
DOI: 10.1039/C9DT02449B

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