Influence of Both Steric Effects and Te···N Intramolecular Nonbonded Interactions on the Stabilization of Organotellurium Compounds Incorporating [2-[1-(3,5-Dimethylphenyl)-2- naphthyl]-4,5-dihydro-4,4-dimethyloxazole]

A series of novel low-valent organotellurium compounds incorporating [2-[1-(3,5-dimethylphenyl)-2-naphthyl]-4,5-dihydro-4,4-dimethyloxazole] (1) stabilized by Te···N nonbonded
interactions have been synthesized. The synthesis has been achieved by the ortholithium
route. The lithium arenetellurolate 3 was obtained by direct metalation of 1 with 1.6 M of
n-BuLi in hexane followed by the insertion of tellurium into the Li−C bond. Oxidation of 3
then afforded the desired ditelluride 4. The reaction of 4 with a stoichiometric amount of
sulfuryl chloride yielded stable tellurenyl(II) chloride 5, whereas the addition of an excess
sulfuryl chloride led to the formation of tellurium(IV) trichloride 6. The stable bromo
compound 7 was obtained by the controlled bromination of 4 with bromine. No tellurium
tribromide formation was observed when the ditelluride was treated with an excess of
bromine. Compound 4 underwent facile reaction with a stoichiometric amount of iodine to
give a stable mono iodo compound (8). The phenyltelluride derivative 9 was obtained by the
treatment of lithiated product 2 with PhTeBr at low temperature. Attempts to synthesize
the symmetrical telluride of the type R2Te (10) by the reaction of 2 with Te(dtc)2 (dtc =
diethyldithiocarbamate) or TeI2 were unsuccessful. All compounds were characterized by
elemental analysis, multinuclear (1H, 13C, 125Te) NMR, and mass spectrometry techniques.
The presence of strong Te···N intramolecular nonbonded interactions in all the compounds
was confirmed by single-crystal X-ray crystallographic studies.