Reactions of chloromethyloxirane and dihalopropanols with chalcogens in basic reducing systems |
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Authors: | A. V. Elaev V. A. Grabel’nykh N. V. Russavskaya E. P. Levanova E. N. Sukhomazova E. R. Zhanchipova L. V. Klyba A. I. Albanov N. A. Korchevin |
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Affiliation: | (1) Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia |
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Abstract: | Chloromethyloxirane and 2,3-dibromopropan-1-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-diyldiseleno 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-aminoethanol. Under analogous conditions 2,3-dibromopropan-1-ol was converted into allyl alcohol with regeneration of elemental selenium. Reductive cleavage of polyselenide oligomers gave Se-methyl derivatives of 2-hydroxypropane-1,3-diselenol. |
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