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Reduction of organic azides by indyl-anions. Isolation and reactivity studies of indium-nitrogen multiple bonds.


ABSTRACT: The synthesis of a new potassium-indyl complex, K[In(NONAr)] (NONAr = [O(SiMe2NAr)2]2-, Ar = 2,6-iPr2C6H3) and its reactivity with organic azides RN3 is reported. When R = 2,6-bis(diphenylmethyl)-4- t Bu-phenyl, a dianionic alkyl-amide ligand is formed via C-H activation across a transient In-Nimide bond. Reducing the size of the R-group to 2,4,6-trimethylphenyl (mesityl, Mes) enables oxidation of the indium and elimination of dinitrogen to afford the imide species, K[In(NONAr)(NMes)]. The anion contains a short In-Nimide bond, shown computationally to contain appreciable multiple bond character. Reaction of isolated imides with an additional equivalent of azide (R = Mes, SiMe3) generates tetrazenido-indium compounds K[In(NONAr){?-N,N'-N4(Mes)(R)-1,4}], shown by X-ray crystallography to contain planar InN4 heterocycles in the anion.

SUBMITTER: Anker MD 

PROVIDER: S-EPMC6349055 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Reduction of organic azides by indyl-anions. Isolation and reactivity studies of indium-nitrogen multiple bonds.

Anker Mathew D MD   Lein Matthias M   Coles Martyn P MP  

Chemical science 20181112 4


The synthesis of a new potassium-indyl complex, K[In(NON<sup>Ar</sup>)] (NON<sup>Ar</sup> = [O(SiMe<sub>2</sub>NAr)<sub>2</sub>]<sup>2-</sup>, Ar = 2,6-<sup>i</sup>Pr<sub>2</sub>C<sub>6</sub>H<sub>3</sub>) and its reactivity with organic azides RN<sub>3</sub> is reported. When R = 2,6-bis(diphenylmethyl)-4- <sup><i>t</i></sup> Bu-phenyl, a dianionic alkyl-amide ligand is formed <i>via</i> C-H activation across a transient In-N<sub>imide</sub> bond. Reducing the size of the R-group to 2,4,6-trime  ...[more]

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