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Synthesis of 2-(5H)-furanones by cyclization of alkyl allene carboxylates in triflic acid. / Mammeri, Oussama Abdelhamid; Baranov, Ilia M.; Ivanov, Alexandr Yu; Boyarskaya, Irina A.; Vasilyev, Aleksander V.

In: Tetrahedron, Vol. 146, 133649, 01.10.2023.

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

Harvard

Mammeri, OA, Baranov, IM, Ivanov, AY, Boyarskaya, IA & Vasilyev, AV 2023, 'Synthesis of 2-(5H)-furanones by cyclization of alkyl allene carboxylates in triflic acid', Tetrahedron, vol. 146, 133649. https://doi.org/10.1016/j.tet.2023.133649, https://doi.org/10.1016/j.tet.2023.133649

APA

Mammeri, O. A., Baranov, I. M., Ivanov, A. Y., Boyarskaya, I. A., & Vasilyev, A. V. (2023). Synthesis of 2-(5H)-furanones by cyclization of alkyl allene carboxylates in triflic acid. Tetrahedron, 146, [133649]. https://doi.org/10.1016/j.tet.2023.133649, https://doi.org/10.1016/j.tet.2023.133649

Vancouver

Mammeri OA, Baranov IM, Ivanov AY, Boyarskaya IA, Vasilyev AV. Synthesis of 2-(5H)-furanones by cyclization of alkyl allene carboxylates in triflic acid. Tetrahedron. 2023 Oct 1;146. 133649. https://doi.org/10.1016/j.tet.2023.133649, https://doi.org/10.1016/j.tet.2023.133649

Author

Mammeri, Oussama Abdelhamid ; Baranov, Ilia M. ; Ivanov, Alexandr Yu ; Boyarskaya, Irina A. ; Vasilyev, Aleksander V. / Synthesis of 2-(5H)-furanones by cyclization of alkyl allene carboxylates in triflic acid. In: Tetrahedron. 2023 ; Vol. 146.

BibTeX

@article{ce407db309df4d1e8f6f71448e22c1e5,
title = "Synthesis of 2-(5H)-furanones by cyclization of alkyl allene carboxylates in triflic acid",
abstract = "Alkyl allene carboxylates [R2(R3)C=C=C(R1)–C(=O)OAlk] in Br{\o}nsted superacid CF3SO3H (triflic acid, TfOH) at room temperature or 70 °C for 30 min are cyclized to form 2-(5H)-furanones in yields up to 83%. The reaction cationic intermediates, O-monoprotonated [R2(R3)C=C=C(R1)–C(=O+H)OAlk] and O,C-diprotonated [R2(R3)C+–CH=C(R1)–C(=O+H)OAlk] forms of starting allenes, have been studied experimentally by NMR and theoretically by DFT calculations. It has been found that the cyclization proceeds via O,C-diprotonated forms of starting allenes.",
keywords = "аллены, фураноны, циклизация, Allene carboxylates, Carbocations, Electrophilic activation, Furanones, Triflic acid",
author = "Mammeri, {Oussama Abdelhamid} and Baranov, {Ilia M.} and Ivanov, {Alexandr Yu} and Boyarskaya, {Irina A.} and Vasilyev, {Aleksander V.}",
note = "Mammeri O.A., Baranov I.M., Ivanov A.Yu., Boyarskay I.A., Vasilyev A.V. Synthesis of 2-(5H)-furanones by cyclization of alkyl allene carboxylated in triflic acid. Tetrahedron, 2023, v. 146, 133649.",
year = "2023",
month = oct,
day = "1",
doi = "10.1016/j.tet.2023.133649",
language = "English",
volume = "146",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Synthesis of 2-(5H)-furanones by cyclization of alkyl allene carboxylates in triflic acid

AU - Mammeri, Oussama Abdelhamid

AU - Baranov, Ilia M.

AU - Ivanov, Alexandr Yu

AU - Boyarskaya, Irina A.

AU - Vasilyev, Aleksander V.

N1 - Mammeri O.A., Baranov I.M., Ivanov A.Yu., Boyarskay I.A., Vasilyev A.V. Synthesis of 2-(5H)-furanones by cyclization of alkyl allene carboxylated in triflic acid. Tetrahedron, 2023, v. 146, 133649.

PY - 2023/10/1

Y1 - 2023/10/1

N2 - Alkyl allene carboxylates [R2(R3)C=C=C(R1)–C(=O)OAlk] in Brønsted superacid CF3SO3H (triflic acid, TfOH) at room temperature or 70 °C for 30 min are cyclized to form 2-(5H)-furanones in yields up to 83%. The reaction cationic intermediates, O-monoprotonated [R2(R3)C=C=C(R1)–C(=O+H)OAlk] and O,C-diprotonated [R2(R3)C+–CH=C(R1)–C(=O+H)OAlk] forms of starting allenes, have been studied experimentally by NMR and theoretically by DFT calculations. It has been found that the cyclization proceeds via O,C-diprotonated forms of starting allenes.

AB - Alkyl allene carboxylates [R2(R3)C=C=C(R1)–C(=O)OAlk] in Brønsted superacid CF3SO3H (triflic acid, TfOH) at room temperature or 70 °C for 30 min are cyclized to form 2-(5H)-furanones in yields up to 83%. The reaction cationic intermediates, O-monoprotonated [R2(R3)C=C=C(R1)–C(=O+H)OAlk] and O,C-diprotonated [R2(R3)C+–CH=C(R1)–C(=O+H)OAlk] forms of starting allenes, have been studied experimentally by NMR and theoretically by DFT calculations. It has been found that the cyclization proceeds via O,C-diprotonated forms of starting allenes.

KW - аллены, фураноны, циклизация

KW - Allene carboxylates

KW - Carbocations

KW - Electrophilic activation

KW - Furanones

KW - Triflic acid

UR - https://www.mendeley.com/catalogue/f937d026-1f00-3600-aa87-eaae16a90a11/

U2 - 10.1016/j.tet.2023.133649

DO - 10.1016/j.tet.2023.133649

M3 - Article

VL - 146

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

M1 - 133649

ER -

ID: 113744507