Diols and epoxides Communication 8. Reactions of isomeric γ-chloro butanol acetates with potassium hydroxide

N. I. Shuikin, M. Bartók, B. Kozma

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Abstract

1. The reactions of 4-chloro-2-butanol acetate (I) and 3-chloro-1-butanol acetate (II) with potassium hydroxide were investigated. From (I) 1,3-epoxybutane is formed in 80-85% yield, but from (II) the yield of 1,3-epoxybutane is low (about 7%), and propene (about 55%), trans-2-buten-1-ol (about 6%), and 3-buten-1-ol (about 17%) are formed. 2. The course of the transformations of a γ-chloro alkanol acetate under the action of caustic alkali is essentially determined by the structure of the compound. For a system with the chlorine atom in a primary position, the main course is the formation of the β-epoxide by the mechanism of intramolecular nucleophilic exchange. In the case of a compound with the chlorine atom in a secondary position the main course is the formation of an olefin and an oxo compound. These two main processes pass through the intermediate stage of a chloroalkoxide. 3. The two main reactions may be accompanied by bimolecular nucleophilic exchange processes-the formation of a 1,3-diol and unsaturated alcohols. In the case of γ-chloro alkanol acetates, with increase in the order of the carbon atom carrying the chlorine atom the intramolecular nucleophilic exchange reaction is displaced toward 1,4- and 1,2-elimination.

Original languageEnglish
Pages (from-to)840-843
Number of pages4
JournalBulletin of the Academy of Sciences, USSR Division of Chemical Science
Volume15
Issue number5
DOIs
Publication statusPublished - May 1966

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Butanols
Chlorine
Acetates
Atoms
Communication
Caustics
1-Butanol
Epoxy Compounds
Alkalies
Alkenes
Ion exchange
Carbon
Alcohols
potassium hydroxide
Epoxide 8

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Diols and epoxides Communication 8. Reactions of isomeric γ-chloro butanol acetates with potassium hydroxide",
abstract = "1. The reactions of 4-chloro-2-butanol acetate (I) and 3-chloro-1-butanol acetate (II) with potassium hydroxide were investigated. From (I) 1,3-epoxybutane is formed in 80-85{\%} yield, but from (II) the yield of 1,3-epoxybutane is low (about 7{\%}), and propene (about 55{\%}), trans-2-buten-1-ol (about 6{\%}), and 3-buten-1-ol (about 17{\%}) are formed. 2. The course of the transformations of a γ-chloro alkanol acetate under the action of caustic alkali is essentially determined by the structure of the compound. For a system with the chlorine atom in a primary position, the main course is the formation of the β-epoxide by the mechanism of intramolecular nucleophilic exchange. In the case of a compound with the chlorine atom in a secondary position the main course is the formation of an olefin and an oxo compound. These two main processes pass through the intermediate stage of a chloroalkoxide. 3. The two main reactions may be accompanied by bimolecular nucleophilic exchange processes-the formation of a 1,3-diol and unsaturated alcohols. In the case of γ-chloro alkanol acetates, with increase in the order of the carbon atom carrying the chlorine atom the intramolecular nucleophilic exchange reaction is displaced toward 1,4- and 1,2-elimination.",
author = "Shuikin, {N. I.} and M. Bart{\'o}k and B. Kozma",
year = "1966",
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T1 - Diols and epoxides Communication 8. Reactions of isomeric γ-chloro butanol acetates with potassium hydroxide

AU - Shuikin, N. I.

AU - Bartók, M.

AU - Kozma, B.

PY - 1966/5

Y1 - 1966/5

N2 - 1. The reactions of 4-chloro-2-butanol acetate (I) and 3-chloro-1-butanol acetate (II) with potassium hydroxide were investigated. From (I) 1,3-epoxybutane is formed in 80-85% yield, but from (II) the yield of 1,3-epoxybutane is low (about 7%), and propene (about 55%), trans-2-buten-1-ol (about 6%), and 3-buten-1-ol (about 17%) are formed. 2. The course of the transformations of a γ-chloro alkanol acetate under the action of caustic alkali is essentially determined by the structure of the compound. For a system with the chlorine atom in a primary position, the main course is the formation of the β-epoxide by the mechanism of intramolecular nucleophilic exchange. In the case of a compound with the chlorine atom in a secondary position the main course is the formation of an olefin and an oxo compound. These two main processes pass through the intermediate stage of a chloroalkoxide. 3. The two main reactions may be accompanied by bimolecular nucleophilic exchange processes-the formation of a 1,3-diol and unsaturated alcohols. In the case of γ-chloro alkanol acetates, with increase in the order of the carbon atom carrying the chlorine atom the intramolecular nucleophilic exchange reaction is displaced toward 1,4- and 1,2-elimination.

AB - 1. The reactions of 4-chloro-2-butanol acetate (I) and 3-chloro-1-butanol acetate (II) with potassium hydroxide were investigated. From (I) 1,3-epoxybutane is formed in 80-85% yield, but from (II) the yield of 1,3-epoxybutane is low (about 7%), and propene (about 55%), trans-2-buten-1-ol (about 6%), and 3-buten-1-ol (about 17%) are formed. 2. The course of the transformations of a γ-chloro alkanol acetate under the action of caustic alkali is essentially determined by the structure of the compound. For a system with the chlorine atom in a primary position, the main course is the formation of the β-epoxide by the mechanism of intramolecular nucleophilic exchange. In the case of a compound with the chlorine atom in a secondary position the main course is the formation of an olefin and an oxo compound. These two main processes pass through the intermediate stage of a chloroalkoxide. 3. The two main reactions may be accompanied by bimolecular nucleophilic exchange processes-the formation of a 1,3-diol and unsaturated alcohols. In the case of γ-chloro alkanol acetates, with increase in the order of the carbon atom carrying the chlorine atom the intramolecular nucleophilic exchange reaction is displaced toward 1,4- and 1,2-elimination.

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