- Synthesis and characterization of N,N′,C-bound organotellurium(IV) and organomercury(II) derivatives
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We report the synthesis and characterization of the first examples of organotellurium (IV)/organomercury(II) derivatives of N,N′,C-chelating aryldiamine ligand, 2-{Me2NCH2CH2N(Me)CH2}C6H4Br (20). The dichalcogenides, [2-{Me2NCH2CH2N(Me)CH2}C6H4Se]2 (24) and [2-{Me2NCH2CH2N(Me)CH2}C6H4Te]2 (25), were prepared by treatment of the corresponding Grignard reagent (21)/organolithium reagent (22) in THF with selenium or tellurium, respectively. Compounds [2-{Me2NCH2CH2N(Me)CH2}C6H4]2Se (26) and [2-{Me2NCH2CH2N(Me)CH2}C6H4]Te(S2CN(CH2CH3)2 (27) were synthesized by the reaction of 21/22 with Se(dtc)2 in 2:1 or Te(dtc)2 (dtc = diethyldithiacarbamate) in 1:1 ratio at room temperature. In contrast, the reaction of 21 with TeI2 afforded an unexpected protonated derivative, [2-{(Me2NH)CH2CH2N(Me)CH2}C6H4TeI]+(I)? (28a). Similarly, the halogenation reactions of 25 with chlorine gas or a solution of bromine in THF afforded protonated derivatives, [2-{(Me2NH)CH2CH2N(Me)CH2}C6H4TeCl3]+(Cl)? (29a) and [2-{(Me2NH)CH2CH2N(Me)CH2}C6H4TeBr3]+(Br) ? (30a), respectively. The organomercury precursors; 2-{Me2NCH2CH2N(Me)CH2}C6H4HgCl0.54/Br0.46 (31) and 2-{Me2NCH2CH2N(Me)CH2}C6H4HgBr (32), were obtained by the reaction of 21 with HgCl2 and HgBr2 in dry THF, respectively. The metathetical reaction of 31with silver azide afforded air- and moisture-stable organomercury azide, 2-{Me2NCH2CH2N(Me)CH2}C6H4HgN3 (33) in 87% yield. The transmetallation reaction of 31 with TeBr4 led to isolation of known o-formylphenyltellurenyl bromide. All the derivatives were characterized by various spectroscopic techniques such as 1H, 13C, 77Se, 125Te, 199Hg NMR spectroscopy, elemental analysis, ES-MS and HRMS studies.
- Singh, Puspendra,Gupta, Anand K.,Sharma, Sagar,Singh, Harkesh B.,Butcher, Ray J.
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supporting information
p. 218 - 228
(2018/08/31)
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- SYNTHESE ET ETUDE DES PROPRIETES SPECTROSCOPIQUES D'HALOGENURES DE BENZENE TELLURENYLE ORTHOCARBONYLES.
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General preparation and chemical properties of ortho carbonyl benzene tellurenyl halides are reported.The cis conformation of the oxygen of the carbonyl group and the tellurium atom is in all cases detected by N M R and I R spectroscopies.
- Piette, J. L.,Pardon, M. C.,Weber, R.,Baiwir, M.,Llabres, G.
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p. 247 - 252
(2007/10/02)
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