Organotellurium compounds involving tellurium(II)-nitrogen bond. Synthesis of arenetellurenamides and their reactions with acetylenes

Abstract

Arenetellurenamides have been prepared by the reaction of arenetellurenyl iodide with lithium amides. The N,N-dialkyl derivatives generally decompose above 0°C, whereas the N,N-disily ones are thermally stable enough to distill or recrystallize unless exposed to air. Attempts to prepare arenetellurenamides via hydrolysis of disilylamides have failed and resulted in only diaryl ditellurides and tellurinic acid anhydrides. The N,N-diisopropylbenzenetellurenamide reacts with terminal acetylenes to give acetylenyl tellurides. N,N-diisopropyl- and N,N-disilyltellurenamides were found to add to dimethyl acetylenedicarboxylate to give a 1:1 adduct. The cis isomer was selectively obtained in high yield after the purification by silica gel column chromatography. It was isomerized by distillation to give a mixture of cis and trans isomers