Reactions of chloromethyloxirane and dihalopropanols with chalcogens in basic reducing systems

Autor: E. N. Sukhomazova, Ekaterina P. Levanova, E. R. Zhanchipova, L. V. Klyba, N. V. Russavskaya, V. A. Grabel’nykh, A. V. Elaev, N. A. Korchevin, A. I. Albanov
Rok vydání: 2008
Předmět:
Zdroj: Russian Journal of Organic Chemistry. 44:505-510
ISSN: 1608-3393
1070-4280
DOI: 10.1134/s1070428008040064
Popis: 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.
Databáze: OpenAIRE