Bis(2,6-dimethoxyphenyl) sulfide, selenide and telluride, and their derivatives

Abstract

2,6-Dimethoxyphenyl derivatives of sulfur, selenium, and tellurium, such as ΦEEΦ, Φ2E, ΦSeH, [MeΦ2E]X (X=MeSO4, ClO4), Φ2EO · xH2O, [Φ2EOR]ClO4, [Φ2EOH]ClO4 (R=Me, Et), Me2SnCl2 · 2Φ2EO (E=S, Se) [Φ=2,6-(MeO)2C6H3; E=S, Se, Te] have been prepared, and their properties compared with common phenyl derivatives. The reaction rates of Φ2E with dimethyl sulfate and butyl bromide increased in the order E=S<Se<Te, which were compared with those of Ph3M and Φ3M, M=P>As>Sb. These reactivities are parallel with the electrochemical oxidation potentials reported for Ph2E and with the first ionization potentials reported for Ph3M. The rate of Φ2Te was faster than that of Ph3P and slightly faster than that of Φ3Sb. From the reactivity of [Φ2E-Me]+ salts with nucleophiles, the E+–Me bond strengths were estimated to increase in the order E=Se<S<Te. The reaction rates of Φ2EO with dimethyl sulfate increased in the order E=S<Se<Te, and the respective rate of Φ2EO was faster than that of Φ2E. The origins of these reactivities and bond strengths are discussed.