Regioselective synthesis of functional tellanes from tellurium tetrahalides and 1-octene

Highly efficient regioselective synthesis of organotellurium compounds based on the reactions of tellurium tetrachloride with 1-alkenes

“…The methoxytelluration reaction in the system CH2Cl2-methanol proceeds at room temperature affording trichloro-(2-methoxyalkyl)-λ 4 -tellanes 5 and 6 in quantitative yield and with higher purity than in the chloroformmethanol mixture. 19,20 We found that tellanes 5 and 6 can be also obtained in quantitative yield by nucleophilic substitution of chlorine atom in tellanes 3 and 4 with alcohols under unusually mild conditions. The reaction proceeded smoothly at room temperature in the systems CH2Cl2-methanol or chloroform-methanol giving tellanes 5 and 6 in quantitative yields.…”

“…[10][11][12][13][14][15] We are making a systematic study of the reactions of tellurium tetrahalides with unsaturated compounds. [16][17][18][19][20][21][22][23][24][25] Recently we have found that methoxytelluration can be accomplished by the reaction of tellurium tetrabromide with 1-hexene in methanol. 17 The reaction proceeded with high regioselectivity to afford Markovnikov's products, tribromo-(2-methoxyhexyl)-λ 4 -tellane.…”

“…Similar methoxytelluration reactions were accomplished with styrene and 1-octene. 18,19 Tellurium tetrachloride cannot be used under similar conditions due to methanolysis of the Te-Cl bond. However, we found that methoxytelluration reaction of tellurium tetrachloride can be carried out in a mixture of chloroform and methanol.…”

“…However, we found that methoxytelluration reaction of tellurium tetrachloride can be carried out in a mixture of chloroform and methanol. 19,20 The present paper is devoted to regioselective synthesis of organotellurium compounds based on chlorotelluration and alkoxytelluration reactions of tellurium tetrachloride with 1-hexene and 1-heptene. Examples of nucleophilic substitution of chlorine atom in trichloro-(2-chloroalkyl)-λ 4 -tellanes with alcohols under unusually mild conditions are discussed.…”