The reaction of chloro(organylthio)acetylenes with alcohols and mercaptans in the presence of their sodium derivatives

A. N. Mirskova; N. V. Lutskaya; I. D. Kalikhman; B. A. Shainyan; M. G. Voronkov

doi:10.1007/BF00924825

The reaction of chloro(organylthio)acetylenes with alcohols and mercaptans in the presence of their sodium derivatives

A. N. Mirskova, N. V. Lutskaya, I. D. Kalikhman, B. A. Shainyan, M. G. Voronkov

Research output: Contribution to journal › Article › peer-review

Abstract

1. Propanol and propylmercaptan regiospecifically add to the triple bond of chloropropylthioacetylene with attack of the nucleophile in the case of propanol at the carbon atom attached to sulfur and in the case of propylmercaptan, at the carbon atom attached to chlorine. 2. The addition of an alcohol occurs stereospecifically with the formation of a cis-adduct, while in the addition of propylmercaptan, cis- and trans-1,2-bis(propylthio)-2-chloroethylenes are formed. 3. The differences in the reaction pathways of sodium propylate and sodium propylthiolate are discussed in the framework of the effect of charge and orbital control on the reactivity of these nucleophiles.

Original language	English
Pages (from-to)	527-530
Number of pages	4
Journal	Bulletin of the Academy of Sciences of the USSR Division of Chemical Science
Volume	28
Issue number	3
DOIs	https://doi.org/10.1007/BF00924825
State	Published - 1 Mar 1979
Externally published	Yes

ASJC Scopus subject areas

General Chemistry

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10.1007/BF00924825

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title = "The reaction of chloro(organylthio)acetylenes with alcohols and mercaptans in the presence of their sodium derivatives",

abstract = "1. Propanol and propylmercaptan regiospecifically add to the triple bond of chloropropylthioacetylene with attack of the nucleophile in the case of propanol at the carbon atom attached to sulfur and in the case of propylmercaptan, at the carbon atom attached to chlorine. 2. The addition of an alcohol occurs stereospecifically with the formation of a cis-adduct, while in the addition of propylmercaptan, cis- and trans-1,2-bis(propylthio)-2-chloroethylenes are formed. 3. The differences in the reaction pathways of sodium propylate and sodium propylthiolate are discussed in the framework of the effect of charge and orbital control on the reactivity of these nucleophiles.",

author = "Mirskova, {A. N.} and Lutskaya, {N. V.} and Kalikhman, {I. D.} and Shainyan, {B. A.} and Voronkov, {M. G.}",

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doi = "10.1007/BF00924825",

language = "English",

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TY - JOUR

T1 - The reaction of chloro(organylthio)acetylenes with alcohols and mercaptans in the presence of their sodium derivatives

AU - Mirskova, A. N.

AU - Lutskaya, N. V.

AU - Kalikhman, I. D.

AU - Shainyan, B. A.

AU - Voronkov, M. G.

PY - 1979/3/1

Y1 - 1979/3/1

N2 - 1. Propanol and propylmercaptan regiospecifically add to the triple bond of chloropropylthioacetylene with attack of the nucleophile in the case of propanol at the carbon atom attached to sulfur and in the case of propylmercaptan, at the carbon atom attached to chlorine. 2. The addition of an alcohol occurs stereospecifically with the formation of a cis-adduct, while in the addition of propylmercaptan, cis- and trans-1,2-bis(propylthio)-2-chloroethylenes are formed. 3. The differences in the reaction pathways of sodium propylate and sodium propylthiolate are discussed in the framework of the effect of charge and orbital control on the reactivity of these nucleophiles.

AB - 1. Propanol and propylmercaptan regiospecifically add to the triple bond of chloropropylthioacetylene with attack of the nucleophile in the case of propanol at the carbon atom attached to sulfur and in the case of propylmercaptan, at the carbon atom attached to chlorine. 2. The addition of an alcohol occurs stereospecifically with the formation of a cis-adduct, while in the addition of propylmercaptan, cis- and trans-1,2-bis(propylthio)-2-chloroethylenes are formed. 3. The differences in the reaction pathways of sodium propylate and sodium propylthiolate are discussed in the framework of the effect of charge and orbital control on the reactivity of these nucleophiles.

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JO - Bulletin of the Academy of Sciences of the USSR Division of Chemical Science

JF - Bulletin of the Academy of Sciences of the USSR Division of Chemical Science

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The reaction of chloro(organylthio)acetylenes with alcohols and mercaptans in the presence of their sodium derivatives

Abstract

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