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Synthesis of Unsaturated 1,6-Diketones and 1,6-Diols from Muconic Acid. / Puzanov, Andrey I.; Zakusilo, Dmitriy N.; Boyarskaya, Irina A.; Spiridonova, Dar’ya V.; Иванов, Александр Юльевич; Kryukova, Mariya A.; Vasilyev, Aleksander V.

In: Journal of Organic Chemistry, Vol. 90, No. 23, 29.05.2025, p. 7555-7566.

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

Harvard

Puzanov, AI, Zakusilo, DN, Boyarskaya, IA, Spiridonova, DV, Иванов, АЮ, Kryukova, MA & Vasilyev, AV 2025, 'Synthesis of Unsaturated 1,6-Diketones and 1,6-Diols from Muconic Acid', Journal of Organic Chemistry, vol. 90, no. 23, pp. 7555-7566. https://doi.org/10.1021/acs.joc.4c02535

APA

Puzanov, A. I., Zakusilo, D. N., Boyarskaya, I. A., Spiridonova, D. V., Иванов, А. Ю., Kryukova, M. A., & Vasilyev, A. V. (2025). Synthesis of Unsaturated 1,6-Diketones and 1,6-Diols from Muconic Acid. Journal of Organic Chemistry, 90(23), 7555-7566. https://doi.org/10.1021/acs.joc.4c02535

Vancouver

Puzanov AI, Zakusilo DN, Boyarskaya IA, Spiridonova DV, Иванов АЮ, Kryukova MA et al. Synthesis of Unsaturated 1,6-Diketones and 1,6-Diols from Muconic Acid. Journal of Organic Chemistry. 2025 May 29;90(23):7555-7566. https://doi.org/10.1021/acs.joc.4c02535

Author

Puzanov, Andrey I. ; Zakusilo, Dmitriy N. ; Boyarskaya, Irina A. ; Spiridonova, Dar’ya V. ; Иванов, Александр Юльевич ; Kryukova, Mariya A. ; Vasilyev, Aleksander V. / Synthesis of Unsaturated 1,6-Diketones and 1,6-Diols from Muconic Acid. In: Journal of Organic Chemistry. 2025 ; Vol. 90, No. 23. pp. 7555-7566.

BibTeX

@article{f7b766cb8ff845f69fefb709bab43c73,
title = "Synthesis of Unsaturated 1,6-Diketones and 1,6-Diols from Muconic Acid",
abstract = "is-,cis-muconic acid (HO2C-CH═CH-CH═CH-CO2H) reacts with arenes in Bro̷nsted superacid TfOH, affording the aromatic acylation products, unsaturated E-,E-1,6-diketones [ArOC-CH═CH-CH═CH-COAr]. These diketones are also obtained in Friedel-Crafts acylation of arenes by muconoyl chloride. The reaction in TfOH proceeds through an intermediate formation of muconic acid O,O-diprotonated form [HO(+HO═C)-CH═CH-CH═CH-C(═OH)+OH], which was investigated experimentally by NMR and theoretically by DFT calculations. Carbonyl reduction of these 1,6-diketones with NaBH4 results in the formation of the corresponding unsaturated diastereomeric E-,E-1,6-diols [Ar(HO)CH-CH═CH-CH═CH-CH(OH)Ar]. Catalytic hydrogenation of carbon-carbon bonds in 1,6-diketones with Pd or Pt on carbon furnishes the corresponding 1,6-diketones (ArOC-CH2CH2CH2CH2-COAr). The studied reactions contribute to the development of organic synthesis on the basis of transformations of muconic acid, which is an important compound in industrial chemistry.",
author = "Puzanov, {Andrey I.} and Zakusilo, {Dmitriy N.} and Boyarskaya, {Irina A.} and Spiridonova, {Dar{\textquoteright}ya V.} and Иванов, {Александр Юльевич} and Kryukova, {Mariya A.} and Vasilyev, {Aleksander V.}",
note = "doi: 10.1021/acs.joc.4c02535",
year = "2025",
month = may,
day = "29",
doi = "10.1021/acs.joc.4c02535",
language = "русский",
volume = "90",
pages = "7555--7566",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "23",

}

RIS

TY - JOUR

T1 - Synthesis of Unsaturated 1,6-Diketones and 1,6-Diols from Muconic Acid

AU - Puzanov, Andrey I.

AU - Zakusilo, Dmitriy N.

AU - Boyarskaya, Irina A.

AU - Spiridonova, Dar’ya V.

AU - Иванов, Александр Юльевич

AU - Kryukova, Mariya A.

AU - Vasilyev, Aleksander V.

N1 - doi: 10.1021/acs.joc.4c02535

PY - 2025/5/29

Y1 - 2025/5/29

N2 - is-,cis-muconic acid (HO2C-CH═CH-CH═CH-CO2H) reacts with arenes in Bro̷nsted superacid TfOH, affording the aromatic acylation products, unsaturated E-,E-1,6-diketones [ArOC-CH═CH-CH═CH-COAr]. These diketones are also obtained in Friedel-Crafts acylation of arenes by muconoyl chloride. The reaction in TfOH proceeds through an intermediate formation of muconic acid O,O-diprotonated form [HO(+HO═C)-CH═CH-CH═CH-C(═OH)+OH], which was investigated experimentally by NMR and theoretically by DFT calculations. Carbonyl reduction of these 1,6-diketones with NaBH4 results in the formation of the corresponding unsaturated diastereomeric E-,E-1,6-diols [Ar(HO)CH-CH═CH-CH═CH-CH(OH)Ar]. Catalytic hydrogenation of carbon-carbon bonds in 1,6-diketones with Pd or Pt on carbon furnishes the corresponding 1,6-diketones (ArOC-CH2CH2CH2CH2-COAr). The studied reactions contribute to the development of organic synthesis on the basis of transformations of muconic acid, which is an important compound in industrial chemistry.

AB - is-,cis-muconic acid (HO2C-CH═CH-CH═CH-CO2H) reacts with arenes in Bro̷nsted superacid TfOH, affording the aromatic acylation products, unsaturated E-,E-1,6-diketones [ArOC-CH═CH-CH═CH-COAr]. These diketones are also obtained in Friedel-Crafts acylation of arenes by muconoyl chloride. The reaction in TfOH proceeds through an intermediate formation of muconic acid O,O-diprotonated form [HO(+HO═C)-CH═CH-CH═CH-C(═OH)+OH], which was investigated experimentally by NMR and theoretically by DFT calculations. Carbonyl reduction of these 1,6-diketones with NaBH4 results in the formation of the corresponding unsaturated diastereomeric E-,E-1,6-diols [Ar(HO)CH-CH═CH-CH═CH-CH(OH)Ar]. Catalytic hydrogenation of carbon-carbon bonds in 1,6-diketones with Pd or Pt on carbon furnishes the corresponding 1,6-diketones (ArOC-CH2CH2CH2CH2-COAr). The studied reactions contribute to the development of organic synthesis on the basis of transformations of muconic acid, which is an important compound in industrial chemistry.

UR - https://www.mendeley.com/catalogue/940d6eee-f068-3390-8b20-affcc7e94b98/

U2 - 10.1021/acs.joc.4c02535

DO - 10.1021/acs.joc.4c02535

M3 - статья

VL - 90

SP - 7555

EP - 7566

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 23

ER -

ID: 137604351