Reactions of chloromethyloxirane and dihalopropanols with chalcogens in basic reducing systems
摘要:
Chloromethyloxirane and 2,3-dibromopropan-l-ol reacted with a solution of selenium or tellurium in the system hydrazin hydrate-potassium hydroxide (K2Se2, K2Te2) to give allyl alcohol; the reaction was accompanied by regeneration of the initial free chalcogen. 1,3-Dichloropropan-2-ol reacted with selenium in the same system to give oligomeric product having a 2-hydroxypropane-1,3-diyidiseleno monomeric unit, while the reaction with tellurium led to the formation of allyl alcohol and almost complete regeneration of initial tellurium. Probable reaction mechanisms are discussed. Polyselenide oligomers containing a hydroxy group in a monomeric unit were formed in reactions of chloromethyloxirane and 1,3-dichloropropan-2-ol with selenium in the system hydrazine hydrate-2-aininoethanol. Under analogous conditions 2,3-dibromopropan-l-ol was converted into allyl alcohol with regeneration of elemental selenium. Reductive cleavage of poly-selenide oligomers gave Se-methyl derivatives of 2-hydroxypropane-1,3-diselenol.