Synthesis of substituted chloroacetylenes from methyl ketones

S. F. Vasilevskii, A. N. Sinyakov, M. S. Shvartsberg, I. L. Kotlyarevskii

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

1. Depending on the conditions, the reaction of methyl aryl ketones with phosphorus pentachloride leads to products from substitution of the carbonyl oxygen by chlorine, αβ-dichlorovinylarenes, or compounds with higher degrees of chlorination. 2. By eliminating a molecule of hydrogen chloride under the influence of an equimolar amount of sodium amide in ammonia, substituted, α,β-dichloroethylenes give high yields of the respective 2-chloroacetylene. 3. The synthesis of a series of ethynyl- and β-chloroethynylpyrazoles from methylpyrazolyl ketones was realized.

Original languageEnglish
Pages (from-to)2134-2138
Number of pages5
JournalBulletin of the Academy of Sciences of the USSR Division of Chemical Science
Volume25
Issue number10
DOIs
Publication statusPublished - 1 Oct 1976
Externally publishedYes

Fingerprint

Ketones
Dichloroethylenes
Hydrochloric Acid
Chlorination
Chlorine
Ammonia
Amides
Phosphorus
Substitution reactions
Sodium
Oxygen
Molecules

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis of substituted chloroacetylenes from methyl ketones. / Vasilevskii, S. F.; Sinyakov, A. N.; Shvartsberg, M. S.; Kotlyarevskii, I. L.

In: Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, Vol. 25, No. 10, 01.10.1976, p. 2134-2138.

Research output: Contribution to journalArticle

Vasilevskii, S. F. ; Sinyakov, A. N. ; Shvartsberg, M. S. ; Kotlyarevskii, I. L. / Synthesis of substituted chloroacetylenes from methyl ketones. In: Bulletin of the Academy of Sciences of the USSR Division of Chemical Science. 1976 ; Vol. 25, No. 10. pp. 2134-2138.
@article{0d413146acd2437cbdfcd31a25f514f6,
title = "Synthesis of substituted chloroacetylenes from methyl ketones",
abstract = "1. Depending on the conditions, the reaction of methyl aryl ketones with phosphorus pentachloride leads to products from substitution of the carbonyl oxygen by chlorine, αβ-dichlorovinylarenes, or compounds with higher degrees of chlorination. 2. By eliminating a molecule of hydrogen chloride under the influence of an equimolar amount of sodium amide in ammonia, substituted, α,β-dichloroethylenes give high yields of the respective 2-chloroacetylene. 3. The synthesis of a series of ethynyl- and β-chloroethynylpyrazoles from methylpyrazolyl ketones was realized.",
author = "Vasilevskii, {S. F.} and Sinyakov, {A. N.} and Shvartsberg, {M. S.} and Kotlyarevskii, {I. L.}",
year = "1976",
month = "10",
day = "1",
doi = "10.1007/BF02659533",
language = "English",
volume = "25",
pages = "2134--2138",
journal = "Russian Chemical Bulletin",
issn = "0568-5230",
publisher = "Consultants Bureau",
number = "10",

}

TY - JOUR

T1 - Synthesis of substituted chloroacetylenes from methyl ketones

AU - Vasilevskii, S. F.

AU - Sinyakov, A. N.

AU - Shvartsberg, M. S.

AU - Kotlyarevskii, I. L.

PY - 1976/10/1

Y1 - 1976/10/1

N2 - 1. Depending on the conditions, the reaction of methyl aryl ketones with phosphorus pentachloride leads to products from substitution of the carbonyl oxygen by chlorine, αβ-dichlorovinylarenes, or compounds with higher degrees of chlorination. 2. By eliminating a molecule of hydrogen chloride under the influence of an equimolar amount of sodium amide in ammonia, substituted, α,β-dichloroethylenes give high yields of the respective 2-chloroacetylene. 3. The synthesis of a series of ethynyl- and β-chloroethynylpyrazoles from methylpyrazolyl ketones was realized.

AB - 1. Depending on the conditions, the reaction of methyl aryl ketones with phosphorus pentachloride leads to products from substitution of the carbonyl oxygen by chlorine, αβ-dichlorovinylarenes, or compounds with higher degrees of chlorination. 2. By eliminating a molecule of hydrogen chloride under the influence of an equimolar amount of sodium amide in ammonia, substituted, α,β-dichloroethylenes give high yields of the respective 2-chloroacetylene. 3. The synthesis of a series of ethynyl- and β-chloroethynylpyrazoles from methylpyrazolyl ketones was realized.

UR - http://www.scopus.com/inward/record.url?scp=51649189115&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=51649189115&partnerID=8YFLogxK

U2 - 10.1007/BF02659533

DO - 10.1007/BF02659533

M3 - Article

AN - SCOPUS:51649189115

VL - 25

SP - 2134

EP - 2138

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

SN - 0568-5230

IS - 10

ER -