Synthesis and properties of the first representatives of terminal acetylenes in 3-imidazoline-1-oxyl 3-oxide series

O. L. Krivenko, S. F. Vasilevskii

Research output: Contribution to journalArticle

Abstract

Method for the synthesis of m-and p-isomers of 4-[2-(ethynylphenyl)vinyl]- 2,2,5,5-tetramethyl-3-imidazoline-1-oxyl 3-oxides by the cross-coupling of 4-[2-(3-iodophenyl)vinyl]-and 4-[2-(4-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3- imidazoline-1-oxyl 3-oxides with (trimethylsilyl)acetylene followed by desilylation was elaborated. The reactions at the CH-fragment of the ethynyl group were performed. The Mannich reaction proceeds with the loss of a spin label, whereas the oxidative homocoupling, with its retention.

Original languageEnglish
Pages (from-to)2123-2126
Number of pages4
JournalRussian Chemical Bulletin
Volume56
Issue number10
DOIs
Publication statusPublished - 1 Oct 2007
Externally publishedYes

Fingerprint

Imidazolines
Alkynes
Oxides
Spin Labels
Acetylene
Isomers

Keywords

  • 3-imidazolinenitroxides
  • Alkynes
  • Nitroxyl radicals
  • The Sonogashira reaction

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis and properties of the first representatives of terminal acetylenes in 3-imidazoline-1-oxyl 3-oxide series. / Krivenko, O. L.; Vasilevskii, S. F.

In: Russian Chemical Bulletin, Vol. 56, No. 10, 01.10.2007, p. 2123-2126.

Research output: Contribution to journalArticle

@article{8a79244a237e46568f59a2e96677bef0,
title = "Synthesis and properties of the first representatives of terminal acetylenes in 3-imidazoline-1-oxyl 3-oxide series",
abstract = "Method for the synthesis of m-and p-isomers of 4-[2-(ethynylphenyl)vinyl]- 2,2,5,5-tetramethyl-3-imidazoline-1-oxyl 3-oxides by the cross-coupling of 4-[2-(3-iodophenyl)vinyl]-and 4-[2-(4-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3- imidazoline-1-oxyl 3-oxides with (trimethylsilyl)acetylene followed by desilylation was elaborated. The reactions at the CH-fragment of the ethynyl group were performed. The Mannich reaction proceeds with the loss of a spin label, whereas the oxidative homocoupling, with its retention.",
keywords = "3-imidazolinenitroxides, Alkynes, Nitroxyl radicals, The Sonogashira reaction",
author = "Krivenko, {O. L.} and Vasilevskii, {S. F.}",
year = "2007",
month = "10",
day = "1",
doi = "10.1007/s11172-007-0333-4",
language = "English",
volume = "56",
pages = "2123--2126",
journal = "Russian Chemical Bulletin",
issn = "1066-5285",
publisher = "Springer New York",
number = "10",

}

TY - JOUR

T1 - Synthesis and properties of the first representatives of terminal acetylenes in 3-imidazoline-1-oxyl 3-oxide series

AU - Krivenko, O. L.

AU - Vasilevskii, S. F.

PY - 2007/10/1

Y1 - 2007/10/1

N2 - Method for the synthesis of m-and p-isomers of 4-[2-(ethynylphenyl)vinyl]- 2,2,5,5-tetramethyl-3-imidazoline-1-oxyl 3-oxides by the cross-coupling of 4-[2-(3-iodophenyl)vinyl]-and 4-[2-(4-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3- imidazoline-1-oxyl 3-oxides with (trimethylsilyl)acetylene followed by desilylation was elaborated. The reactions at the CH-fragment of the ethynyl group were performed. The Mannich reaction proceeds with the loss of a spin label, whereas the oxidative homocoupling, with its retention.

AB - Method for the synthesis of m-and p-isomers of 4-[2-(ethynylphenyl)vinyl]- 2,2,5,5-tetramethyl-3-imidazoline-1-oxyl 3-oxides by the cross-coupling of 4-[2-(3-iodophenyl)vinyl]-and 4-[2-(4-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3- imidazoline-1-oxyl 3-oxides with (trimethylsilyl)acetylene followed by desilylation was elaborated. The reactions at the CH-fragment of the ethynyl group were performed. The Mannich reaction proceeds with the loss of a spin label, whereas the oxidative homocoupling, with its retention.

KW - 3-imidazolinenitroxides

KW - Alkynes

KW - Nitroxyl radicals

KW - The Sonogashira reaction

UR - http://www.scopus.com/inward/record.url?scp=41049086865&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=41049086865&partnerID=8YFLogxK

U2 - 10.1007/s11172-007-0333-4

DO - 10.1007/s11172-007-0333-4

M3 - Article

VL - 56

SP - 2123

EP - 2126

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

SN - 1066-5285

IS - 10

ER -