Issue 4, 2013

Organoantimony(iii) compounds containing (imino)aryl ligands of the type 2-(RN[double bond, length as m-dash]CH)C6H4 (R = 2′,4′,6′-Me3C6H2, 2′,6′-iPr2C6H3): bromides and chalcogenides

Abstract

The reaction of 2-(RN[double bond, length as m-dash]CH)C6H4MgBr [R = 2′,4′,6′-Me3C6H2 (R1), 2′,6′-iPr2C6H3 (R2)] [prepared from 2-(R1N[double bond, length as m-dash]CH)C6H4Br (1) or 2-(R2N[double bond, length as m-dash]CH)C6H4Br (2) and Mg] with SbCl3 in a 2 : 1 and 1 : 1 molar ratio followed by treatment with an aqueous KBr solution gave [2-(R1N[double bond, length as m-dash]CH)C6H4]2SbBr (3) and [2-(R2N[double bond, length as m-dash]CH)C6H4]2SbBr (4) as well as [2-(R1N[double bond, length as m-dash]CH)C6H4]SbBr2 (6) and [2-(R2N[double bond, length as m-dash]CH)C6H4]SbBr2 (7). Treatment of 4 with Na2S·9H2O provided the dinuclear [{2-(R2N[double bond, length as m-dash]CH)C6H4}2Sb]2S (5). Heterocyclic species, i.e. the oxide cyclo-[{2-(R2N[double bond, length as m-dash]CH)C6H4}SbO]3 (8) and the sulfides cyclo-[{2-(R1N[double bond, length as m-dash]CH)C6H4}SbS]2 (9) and cyclo-[{2-(R2N[double bond, length as m-dash]CH)C6H4}SbS]2 (10), were obtained by reacting dibromides 6 and 7 with KOH and Na2S·9H2O, respectively, in a water–toluene solvent mixture. The sulfide 10 reacted with [W(CO)5(thf)] to yield the heterometallic complex cyclo-[{2-(R2N[double bond, length as m-dash]CH)C6H4}SbS]2[W(CO)5] (11). The compounds were characterised by multinuclear NMR spectroscopy in solution, mass spectrometry and IR spectroscopy in the solid state. The molecular structures of 4, 5, 6·CHCl3, 7, 9·CH2Cl2, 10 and 11·0.25CH3OH were established by single-crystal X-ray diffraction. Theoretical calculations using DFT methods were carried out on bromide 7 and the geometrical isomers of its dimer association as well as the geometrical isomers of sulfide 10 and its monomer.

Graphical abstract: Organoantimony(iii) compounds containing (imino)aryl ligands of the type 2-(RN [[double bond, length as m-dash]] CH)C6H4 (R = 2′,4′,6′-Me3C6H2, 2′,6′-iPr2C6H3): bromides and chalcogenides

Supplementary files

Article information

Article type
Paper
Submitted
19 Oct 2012
Accepted
05 Nov 2012
First published
06 Nov 2012

Dalton Trans., 2013,42, 1144-1158

Organoantimony(III) compounds containing (imino)aryl ligands of the type 2-(RN[double bond, length as m-dash]CH)C6H4 (R = 2′,4′,6′-Me3C6H2, 2′,6′-iPr2C6H3): bromides and chalcogenides

A. M. Preda, C. I. Raţ, C. Silvestru, H. J. Breunig, H. Lang, T. Rüffer and M. Mehring, Dalton Trans., 2013, 42, 1144 DOI: 10.1039/C2DT32494F

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