New approaches to synthesis of unsaturated organochalcogen compounds with two different chalcogen atoms

Two approaches to synthesis of bis-chalcogenyl derivatives of propene with two different chalcogen atoms are proposed. Reaction of 2,3-dichloro-1-propene with two different chalcogen nucleophiles PhY − (Y = S, Se) results in a mixture of two products with two identical chalcogen atoms and two products with different ones. The reactivity of PhY − anions under the reaction conditions (60°C) practically does not depend on the Y nature. Reaction of anions RY − (Y = S, Se, Te) with the products of the reaction of 2,3-dichloro-1-propene and organic chalcogenides in the hydrazine hydrate-alkali medium affords the target unsaturated chalcogen-containing compounds with two different chalcogen atoms, 1,2-bis(organylchalcogenyl) propenes in up to 73% yield.