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Synthesis of sulfur compounds by the aid of vinyl ethers and acetylene. Communication 8. General method for the synthesis of 2-alkoxyethanethiols

 

作者: M.F.Shostakovsky,   E.N.Prilezhaeva,   E.S.Shapiro,  

 

期刊: Bulletin of the Academy of Sciences of the USSR, Division of chemical science  (Springer Available online 2005)
卷期: Volume 3, issue 2  

页码: 245-253

 

ISSN:0568-5230

 

年代: 2005

 

DOI:10.1007/BF01177620

 

出版商: Springer_US-Boston

 

数据来源: Springer

 

摘要:

1.Reaction of hydrogen sulfide with ethyl, propyl, isopropyl, isobutyl, octyl, isopentyl, and eyclohexyl vinyl ethers yielded 2-talkoxyethaiethiols and mixtures of sulfides containing various proportions of the isomeric dialkoxy diethyl sulfides. Addition products formed in violation of Markovnikov's rule predominated in the reaction mixtures, particularly in the case of ethers having normal alkyl radicals. Ethers having branched (isopentyl) and cyclic (cyclohexyl) radicals gave particularly high yields of “normal” addition products.2.A general method is given for the synthesis of 2-alkoxyethanethiols ROCH2,CH2SH in 55–80% yield from the corresponding vinyl ethers.3.It is sugganti-Markovaikovsted that the ratio of Markovnikov and anti-Markovnikov addition products is related to the tendency of the vinyl ether to react by an ionic mech

 

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