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5,5,5-Trichloropent-3-en-one as a Precursor of 1,3-Bi-centered Electrophile in Reactions with Arenes in Brønsted Superacid CF3SO3H. Synthesis of 3-Methyl-1-trichloromethylindenes. / Shershnev, Ivan A.; Boyarskaya, Irina A.; Vasilyev, Aleksander V.

In: Molecules, Vol. 27, No. 19, 6675, 07.10.2022.

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

Harvard

Shershnev, IA, Boyarskaya, IA & Vasilyev, AV 2022, '5,5,5-Trichloropent-3-en-one as a Precursor of 1,3-Bi-centered Electrophile in Reactions with Arenes in Brønsted Superacid CF3SO3H. Synthesis of 3-Methyl-1-trichloromethylindenes', Molecules, vol. 27, no. 19, 6675. https://doi.org/10.3390/molecules27196675

APA

Shershnev, I. A., Boyarskaya, I. A., & Vasilyev, A. V. (2022). 5,5,5-Trichloropent-3-en-one as a Precursor of 1,3-Bi-centered Electrophile in Reactions with Arenes in Brønsted Superacid CF3SO3H. Synthesis of 3-Methyl-1-trichloromethylindenes. Molecules, 27(19), [6675]. https://doi.org/10.3390/molecules27196675

Vancouver

Shershnev IA, Boyarskaya IA, Vasilyev AV. 5,5,5-Trichloropent-3-en-one as a Precursor of 1,3-Bi-centered Electrophile in Reactions with Arenes in Brønsted Superacid CF3SO3H. Synthesis of 3-Methyl-1-trichloromethylindenes. Molecules. 2022 Oct 7;27(19). 6675. https://doi.org/10.3390/molecules27196675

Author

Shershnev, Ivan A. ; Boyarskaya, Irina A. ; Vasilyev, Aleksander V. / 5,5,5-Trichloropent-3-en-one as a Precursor of 1,3-Bi-centered Electrophile in Reactions with Arenes in Brønsted Superacid CF3SO3H. Synthesis of 3-Methyl-1-trichloromethylindenes. In: Molecules. 2022 ; Vol. 27, No. 19.

BibTeX

@article{0fef8005fce849c49975d64e3ec59023,
title = "5,5,5-Trichloropent-3-en-one as a Precursor of 1,3-Bi-centered Electrophile in Reactions with Arenes in Br{\o}nsted Superacid CF3SO3H. Synthesis of 3-Methyl-1-trichloromethylindenes",
abstract = "Reactions of 5,5,5-trichloropent-3-en-2-one Cl3CCH=CHC(=O)Me with arenes in Br{\o}nsted superacid CF3SO3H at room temperature for 2 h–5 days afford 3-methyl-1-trichloromethylindenes, a novel class of indene derivatives. The key reactive intermediate, O-protonated form of starting compound Cl3CCH=CHC(=OH+)Me, has been studied experimentally by NMR in CF3SO3H and theoretically by DFT calculations. The reaction proceeds through initial hydroarylation of the carbon-carbon double bond of starting CCl3-enone, followed by cyclization onto the O-protonated carbonyl group, leading to target indenes. In general, 5,5,5-trichloropent-3-en-2-one in CF3SO3H acts as a 1,3-bi-centered electrophile.",
keywords = "carbocations, enones, Friedel-Crafts reaction, indenes, triflic acid",
author = "Shershnev, {Ivan A.} and Boyarskaya, {Irina A.} and Vasilyev, {Aleksander V.}",
note = "Shershnev, I.A.; Boyarskaya, I.A.; Vasilyev, A.V. 5,5,5-Trichloropent-3-en-one as a Precursor of 1,3-Bi-centered Electrophile in Reactions with Arenes in Br{\o}nsted Superacid CF3SO3H. Synthesis of 3-Methyl-1-trichloromethylindenes. Molecules 2022, 27, 6675. https://doi.org/10.3390/molecules27196675",
year = "2022",
month = oct,
day = "7",
doi = "10.3390/molecules27196675",
language = "English",
volume = "27",
journal = "Molecules",
issn = "1420-3049",
publisher = "MDPI AG",
number = "19",

}

RIS

TY - JOUR

T1 - 5,5,5-Trichloropent-3-en-one as a Precursor of 1,3-Bi-centered Electrophile in Reactions with Arenes in Brønsted Superacid CF3SO3H. Synthesis of 3-Methyl-1-trichloromethylindenes

AU - Shershnev, Ivan A.

AU - Boyarskaya, Irina A.

AU - Vasilyev, Aleksander V.

N1 - Shershnev, I.A.; Boyarskaya, I.A.; Vasilyev, A.V. 5,5,5-Trichloropent-3-en-one as a Precursor of 1,3-Bi-centered Electrophile in Reactions with Arenes in Brønsted Superacid CF3SO3H. Synthesis of 3-Methyl-1-trichloromethylindenes. Molecules 2022, 27, 6675. https://doi.org/10.3390/molecules27196675

PY - 2022/10/7

Y1 - 2022/10/7

N2 - Reactions of 5,5,5-trichloropent-3-en-2-one Cl3CCH=CHC(=O)Me with arenes in Brønsted superacid CF3SO3H at room temperature for 2 h–5 days afford 3-methyl-1-trichloromethylindenes, a novel class of indene derivatives. The key reactive intermediate, O-protonated form of starting compound Cl3CCH=CHC(=OH+)Me, has been studied experimentally by NMR in CF3SO3H and theoretically by DFT calculations. The reaction proceeds through initial hydroarylation of the carbon-carbon double bond of starting CCl3-enone, followed by cyclization onto the O-protonated carbonyl group, leading to target indenes. In general, 5,5,5-trichloropent-3-en-2-one in CF3SO3H acts as a 1,3-bi-centered electrophile.

AB - Reactions of 5,5,5-trichloropent-3-en-2-one Cl3CCH=CHC(=O)Me with arenes in Brønsted superacid CF3SO3H at room temperature for 2 h–5 days afford 3-methyl-1-trichloromethylindenes, a novel class of indene derivatives. The key reactive intermediate, O-protonated form of starting compound Cl3CCH=CHC(=OH+)Me, has been studied experimentally by NMR in CF3SO3H and theoretically by DFT calculations. The reaction proceeds through initial hydroarylation of the carbon-carbon double bond of starting CCl3-enone, followed by cyclization onto the O-protonated carbonyl group, leading to target indenes. In general, 5,5,5-trichloropent-3-en-2-one in CF3SO3H acts as a 1,3-bi-centered electrophile.

KW - carbocations

KW - enones

KW - Friedel-Crafts reaction

KW - indenes

KW - triflic acid

UR - http://www.scopus.com/inward/record.url?scp=85139887289&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/a91a32be-b6d0-3b77-a609-62d5663f56bd/

U2 - 10.3390/molecules27196675

DO - 10.3390/molecules27196675

M3 - Article

C2 - 36235211

AN - SCOPUS:85139887289

VL - 27

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 19

M1 - 6675

ER -

ID: 100074256