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Acid-catalyzed decomposition and stability of diazofuranones : Experimental and mechanistic study. / Semenok, Dmitrii; Mereshchenko, Andrey S.; Medvedev, Jury; Visentin, Giorgio.

In: Journal of Physical Organic Chemistry, Vol. 33, No. 3, e4038, 01.03.2020.

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

Harvard

Semenok, D, Mereshchenko, AS, Medvedev, J & Visentin, G 2020, 'Acid-catalyzed decomposition and stability of diazofuranones: Experimental and mechanistic study', Journal of Physical Organic Chemistry, vol. 33, no. 3, e4038. https://doi.org/10.1002/poc.4038

APA

Semenok, D., Mereshchenko, A. S., Medvedev, J., & Visentin, G. (2020). Acid-catalyzed decomposition and stability of diazofuranones: Experimental and mechanistic study. Journal of Physical Organic Chemistry, 33(3), [e4038]. https://doi.org/10.1002/poc.4038

Vancouver

Semenok D, Mereshchenko AS, Medvedev J, Visentin G. Acid-catalyzed decomposition and stability of diazofuranones: Experimental and mechanistic study. Journal of Physical Organic Chemistry. 2020 Mar 1;33(3). e4038. https://doi.org/10.1002/poc.4038

Author

Semenok, Dmitrii ; Mereshchenko, Andrey S. ; Medvedev, Jury ; Visentin, Giorgio. / Acid-catalyzed decomposition and stability of diazofuranones : Experimental and mechanistic study. In: Journal of Physical Organic Chemistry. 2020 ; Vol. 33, No. 3.

BibTeX

@article{8d9255660f3a4977b8ded779a7cfec71,
title = "Acid-catalyzed decomposition and stability of diazofuranones: Experimental and mechanistic study",
abstract = "Reactions of substituted 4-diazotetrahydrofurane-3-ones with various acids (pKa < 3) irrespective of acid strength give rise to elimination of nitrogen with subsequent 1,2-nucleophilic migration of aryl (alkyl) groups from C-5 to C-4 position of heterocyclic core with quantitative formation of regioisomeric 3(2Н)furanones (yields up to 99%). Regioselectivity of this acid-catalyzed process increases with the decreasing of solvent polarity and strongly depends on the nature of substituents in the aryl groups. The suggested mechanism of this reaction via intermediate RN2 + cation was confirmed by density functional theory (DFT) calculations at the PBE0/6-31+G(d) functional due to good agreement between calculated and experimental data on the acid stability of diazoketones in different solvents.",
keywords = "1,2-nucleophilic rearrangement, 3(2H)furanones, carbocations, diazo compounds, super acids, THERMOLYSIS, TOTAL ENERGIES, SET MODEL CHEMISTRY",
author = "Dmitrii Semenok and Mereshchenko, {Andrey S.} and Jury Medvedev and Giorgio Visentin",
year = "2020",
month = mar,
day = "1",
doi = "10.1002/poc.4038",
language = "English",
volume = "33",
journal = "Journal of Physical Organic Chemistry",
issn = "0894-3230",
publisher = "Wiley-Blackwell",
number = "3",

}

RIS

TY - JOUR

T1 - Acid-catalyzed decomposition and stability of diazofuranones

T2 - Experimental and mechanistic study

AU - Semenok, Dmitrii

AU - Mereshchenko, Andrey S.

AU - Medvedev, Jury

AU - Visentin, Giorgio

PY - 2020/3/1

Y1 - 2020/3/1

N2 - Reactions of substituted 4-diazotetrahydrofurane-3-ones with various acids (pKa < 3) irrespective of acid strength give rise to elimination of nitrogen with subsequent 1,2-nucleophilic migration of aryl (alkyl) groups from C-5 to C-4 position of heterocyclic core with quantitative formation of regioisomeric 3(2Н)furanones (yields up to 99%). Regioselectivity of this acid-catalyzed process increases with the decreasing of solvent polarity and strongly depends on the nature of substituents in the aryl groups. The suggested mechanism of this reaction via intermediate RN2 + cation was confirmed by density functional theory (DFT) calculations at the PBE0/6-31+G(d) functional due to good agreement between calculated and experimental data on the acid stability of diazoketones in different solvents.

AB - Reactions of substituted 4-diazotetrahydrofurane-3-ones with various acids (pKa < 3) irrespective of acid strength give rise to elimination of nitrogen with subsequent 1,2-nucleophilic migration of aryl (alkyl) groups from C-5 to C-4 position of heterocyclic core with quantitative formation of regioisomeric 3(2Н)furanones (yields up to 99%). Regioselectivity of this acid-catalyzed process increases with the decreasing of solvent polarity and strongly depends on the nature of substituents in the aryl groups. The suggested mechanism of this reaction via intermediate RN2 + cation was confirmed by density functional theory (DFT) calculations at the PBE0/6-31+G(d) functional due to good agreement between calculated and experimental data on the acid stability of diazoketones in different solvents.

KW - 1,2-nucleophilic rearrangement

KW - 3(2H)furanones

KW - carbocations

KW - diazo compounds

KW - super acids

KW - THERMOLYSIS

KW - TOTAL ENERGIES

KW - SET MODEL CHEMISTRY

UR - http://www.scopus.com/inward/record.url?scp=85076159973&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/00a96c1f-0f2c-378e-8549-7ae7dea09e50/

U2 - 10.1002/poc.4038

DO - 10.1002/poc.4038

M3 - Article

AN - SCOPUS:85076159973

VL - 33

JO - Journal of Physical Organic Chemistry

JF - Journal of Physical Organic Chemistry

SN - 0894-3230

IS - 3

M1 - e4038

ER -

ID: 51276851