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.

Original language	English
Pages (from-to)	2123-2126
Number of pages	4
Journal	Russian Chemical Bulletin
Volume	56
Issue number	10
DOIs	https://doi.org/10.1007/s11172-007-0333-4
Publication status	Published - 1 Oct 2007
Externally published	Yes

Keywords

3-imidazolinenitroxides
Alkynes
Nitroxyl radicals
The Sonogashira reaction

ASJC Scopus subject areas

Chemistry(all)

Access to Document

10.1007/s11172-007-0333-4

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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 = oct,

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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",

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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

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