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3 article(s) from Yagupolskii, Yurii L

1,2-Difluoroethylene (HFO-1132): synthesis and chemistry

Liubov V. Sokolenko,
Taras M. Sokolenko and
Yurii L. Yagupolskii

Beilstein J. Org. Chem. 2024, 20, 1955–1966, doi:10.3762/bjoc.20.171

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Graphical Abstract

Scheme 1: 1,2-Difluoroethylene synthesis from HFO-1123.

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Scheme 2: 1,2-Difluoroethylene synthesis from CFC-112 and HCFC-132.

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Scheme 3: 1,2-Difluoroethylene synthesis from HFC-143.

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Scheme 4: 1,2-Difluoroethylene synthesis from HCFC-142 via HCFC-142a.

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Scheme 5: 1,2-Difluoroethylene synthesis from CFO-1112.

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Scheme 6: 1,2-Difluoroethylene synthesis from 1,2-dichloroethylene.

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Scheme 7: 1,2-Difluoroethylene synthesis from perfluoropropyl vinyl ether.

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Scheme 8: Deuteration reaction of 1,2-difluoroethylene.

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Scheme 9: Halogen addition to 1,2-difluoroethylene.

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Scheme 10: Hypohalite addition to 1,2-difluoroethylene.

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Scheme 11: N-Bromobis(trifluoromethyl)amine addition to 1,2-difluoroethylene.

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Scheme 12: N-Chloroimidobis(sulfonyl fluoride) addition to 1,2-difluoroethylene.

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Scheme 13: Trichlorosilane addition to 1,2-difluoroethylene.

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Scheme 14: SF₅Br addition to 1,2-difluoroethylene.

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Scheme 15: PCl₃/O₂ addition to 1,2-difluoroethylene.

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Scheme 16: Reaction of tetramethyldiarsine with 1,2-difluoroethylene.

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Scheme 17: Reaction of trichlorofluoromethane with 1,2-difluoroethylene.

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Scheme 18: Addition of perfluoroalkyl iodides to 1,2-difluoroethylene.

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Scheme 19: Cyclopropanation of 1,2-difluoroethylene.

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Scheme 20: Diels–Alder reaction of 1,2-difluoroethylene and hexachlorocyclopentadiene.

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Scheme 21: Cycloaddition reaction of 1,2-difluoroethylene and fluorinated ketones.

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Scheme 22: Cycloaddition reaction of 1,2-difluoroethylene and perfluorinated aldehydes.

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Scheme 23: Photochemical cycloaddition of 1,2-difluoroethylene and hexafluorodiacetyl.

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Scheme 24: Reaction of 1,2-difluoroethylene with difluorosilylene.

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Scheme 25: Reaction of 1,2-difluoroethylene with aryl iodides.

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Review

Published 12 Aug 2024

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(E,Z)-1,1,1,4,4,4-Hexafluorobut-2-enes: hydrofluoroolefins halogenation/dehydrohalogenation cascade to reach new fluorinated allene

Nataliia V. Kirij,
Andrey A. Filatov,
Yurii L. Yagupolskii,
Sheng Peng and
Lee Sprague

Beilstein J. Org. Chem. 2024, 20, 452–459, doi:10.3762/bjoc.20.40

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Scheme 1: Synthesis of 2,3-dibromo-1,1,1,4,4,4-hexafluorobutane (2).

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Scheme 2: Synthesis of (E)-butene 3a.

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Scheme 3: Isomerization reaction of (E)-butene 3a to (Z)-butene 3b.

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Scheme 4: Synthesis of 2-chloro-3-iodo-1,1,1,4,4,4-hexafluorobutane (5).

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Scheme 5: Dehydrohalogenation reaction of 2-chloro-3-iodo-1,1,1,4,4,4-hexafluorobutane (5).

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Scheme 6: The reaction of silane 8 with I₂/KF.

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Scheme 7: The reaction of 3a with iPrMgCl and 4-fluorobenzaldehyde (9).

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Scheme 8: The reaction of olefin 3a with iPrMgCl.

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Scheme 9: The reaction of (E)-butene 3a with BuLi.

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Scheme 10: The reaction of allene 11 with bromine.

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Scheme 11: The reaction of allene 11 with ICl.

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Scheme 12: Synthesis of 2,3-dibromo-2-chloro-1,1,1,4,4,4-hexafluorobutane (16).

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Scheme 13: Synthesis of (Z, E)-2-bromo-3-chloro-1,1,1,4,4,4-hexafluorobut-2-enes (17a,b).

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Scheme 14: The reaction of olefins 17a,b with BuLi.

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Full Research Paper

Published 27 Feb 2024

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A novel family of (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids – analogues of α-amino acids

Natalia V. Pavlenko,
Tatiana I. Oos,
Yurii L. Yagupolskii,
Igor I. Gerus,
Uwe Doeller and
Lothar Willms

Beilstein J. Org. Chem. 2014, 10, 722–731, doi:10.3762/bjoc.10.66

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Scheme 1: Synthesis of (trifluoromethyl)phosphinic acid (1) and ethyl and isopropyl esters 2–4. Reagents and ...

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Scheme 2: Three-component Kabachnik–Fields reaction of CF₃(H)P(O)(OiPr) (2) with formaldehyde and dibenzylami...

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Scheme 3: Three-component synthesis of CF₃ containing α-aminophosphinic acids 14a,b. Reagents and conditions:...

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Scheme 4: Interaction of the acid 1 with tert-butyl benzylidenecarbamate (21). Reagents and conditions: i) an...

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Scheme 5: Interaction of the acids 1 and 6 with ethyl 2-[(tert-butoxycarbonyl)imino]acetate (22). Reagents an...

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Scheme 6: Transformation of the ester 24 into the appropriate free acid 25. Reagents and conditions: i) two f...

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Scheme 7: Reaction of the acids (1) and (6) with methyl 2-imino-3-methylbutanoate (26). Reagents and conditio...

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Scheme 8: Interaction of the acid 1 with ethyl 2-(tert-butoxycarbonylamino)acrylate (29). Reagents and condit...

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Scheme 9: Interaction of a mixture of the esters 3 and 4 with 2-acetamidoacrylic acid (33). Reagents and cond...

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Scheme 10: Interaction of a mixture of the acid 1 with diethyl acetaminomethylenemalonate (38). Reagents and c...

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Published 26 Mar 2014

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