Abstract
The reaction of tellurium tetrachloride with acetylene proceeds in a stereospecific anti-addition manner to afford the novel products E-2-chlorovinyltellurium trichloride and E,E-bis(2-chlorovinyl)tellurium dichloride. Reaction conditions for the selective preparation of each of these products were found. The latter was obtained in 90% yield in CHCl3 under a pressure of acetylene of 10–15 atm, whereas the former product was formed in up to 72% yield in CCl4 under a pressure of acetylene of 1–3 atm. Synthesis of the previously unknown E,E-bis(2-chlorovinyl) telluride, E,E-bis(2-chlorovinyl) ditelluride, E-2-chlorovinyl 1,2,2-trichloroethyl telluride and E,E-bis(2-chlorovinyl)-tellurium dibromide is described.
Highlights
Selenium was considered a poison for many years, until Schwarz and Foltz identified it as an essential micronutrient for mammals, including human beings [1]
The present paper describes electrophilic addition of tellurium tetrachloride to acetylene
In a letter [42] we briefly reported our preliminary results on studies of the reaction of tellurium tetrachloride with acetylene and the formation of a bisadduct, the previously unknown E,E-bis(2-chlorovinyl)tellurium dichloride (1), in 62% yield
Summary
Selenium was considered a poison for many years, until Schwarz and Foltz identified it as an essential micronutrient for mammals, including human beings [1]. Tellurium was regarded a poison for many years until non-toxic organotellurium compounds with high biological activity were found [2,3,4,5,6,7,8]. It has been shown later that the reactions of TeCl4 with phenylacetylene, diphenylacetylene and alkylphenylacetylenes proceed in highly regiospecific and stereospecific manner via syn-addition to afford the products of. It is worth noting that compounds with high biological (antioxidative and antimetastatic) activity were found among the adducts of TeCl4 with acetylenes [3]. Reactions of inorganic compounds with acetylene by convenient procedures giving high yields of target products may find useful applications, in organic synthesis, but in industry as well
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