TITLE:
Investigation of Synthesis of Functionally Substituted Endiines and Their Chemical and Microbiological Conversion
AUTHORS:
M. G. Veliyev, M. A. Salmanov, M. I. Shatirova, S. R. Aliyeva, L. N. Bunyatova
KEYWORDS:
Substitution Reaction; Endiine Diols; Chemical Methods; Oxidation of Diols; Hydrolysis of Epoxydiine; Microbiological Hydrolysis; Micromycetes
JOURNAL NAME:
International Journal of Organic Chemistry,
Vol.3 No.3A,
November
5,
2013
ABSTRACT: The methods of preparation of endiine and endiallene diols by interaction of cis-1,4-dibrombutene and cis-1,4-dichlor-rbutene with monosubstituted acetylene alcohols in presence of the catalytic systems consisting of one-iodide copper, triethylamine and K2СО3 in a medium of dimethylformamide have been developed. It has been shown that unlike 1,4-dibrombutene, the nucleophilic substitution reaction with 1,4-dichlorbutene proceeds by acetylene-allene isomerization with formation of endiallene diols. It has been established that the endiine diols can be used in thin organic synthesis (in the reactions of oxidation, splitting, dehydration, epoxidation, hydrolysis, 1,2-cycloaddition and hypochlorination) with the aim of preparation of practically useful substances. It has been revealed during hydrolysis of epoxide compounds by the chemical and microbiological methods that in the course of microbiological hydrolysis (Aspеrgillus niger), the optically active trans-structured diols are formed.