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Issue 25, 2014
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Unusual formation of a N-heterocyclic germylene via homolytic cleavage of a C–C bond

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Abstract

Reaction of the monoanionic radical salt IP˙K+ (IP = (Py)CH(=NR); Py = C5H4N, R = 2,6-iPr2C6H3; α-iminopyridine) with GeCl2(dioxane) afforded compound (IPGeCl)2 (1) which produced red blocks of IPGe: (2), when treated with KC8 in toluene. 1 is a digermylene formed via C–C coupling between two carbon-centered radicals. 2 can be considered as an analogue of a N-heterocyclic carbene, which exhibits a five-membered GeC2N2 ring with one C[double bond, length as m-dash]C double bond. 2 is formed by two-electron reduction of 1 with cleavage of the two Ge–Cl bonds and the central C–C single bond.

Graphical abstract: Unusual formation of a N-heterocyclic germylene via homolytic cleavage of a C–C bond

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Article information


Submitted
11 Jan 2014
Accepted
01 Feb 2014
First published
03 Feb 2014

Chem. Commun., 2014,50, 3356-3358
Article type
Communication
Author version available

Unusual formation of a N-heterocyclic germylene via homolytic cleavage of a C–C bond

Y. Li, K. C. Mondal, P. Stollberg, H. Zhu, H. W. Roesky, R. Herbst-Irmer, D. Stalke and H. Fliegl, Chem. Commun., 2014, 50, 3356
DOI: 10.1039/C4CC00251B

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