Tetrahedron, volume 72, issue 32, pages 4835-4844

Protonation and transformations of α-diazo-β-dicarbonyl compounds in superacids: generation of the strongest carbon-centered cationic electrophiles at the protonation of diazomalonates in Friedel–Crafts reactions

Satumov Eugeniy T 1
Nilov Denis I 1
Sandzhieva Maria A 2, 3, 4
Boyarskaya Irina A 1
Publication typeJournal Article
Publication date2016-08-01
Journal: Tetrahedron
Quartile SCImago
Q2
Quartile WOS
Q3
Impact factor2.1
ISSN00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Protonation of diazodiketones N2C(COR)2 in Bronsted superacids (TfOH, FSO3H, TfOH–SbF5) gives rise to stable and non-reactive O,O-diprotonated at carbonyl oxygens species N2C(C( OH+)R)2, which were studied by means of 1H and 13C NMR. Diazomalonates N2C(CO2Alk)2, contrary to diazodiketones, react with TfOH or HF, releasing nitrogen and producing triflates of oxymalonates TfOCH(CO2Alk)2 or fluoromalonates FCH(CO2Alk)2, respectively. Diazoketoesters N2C(COR)(CO2Alk) react in the same way only with TfOH, but not with HF. The reactions of diazomalonates with arenes ArH (benzene, toluene, xylenes) in TfOH solution yield corresponding Friedel–Crafts reaction products ArCH(CO2Alk)2. According to performed DFT calculations, trication +CH(C( OH+)OMe)2, a possible intermediate, which is derived from protonation of dimethyl diazomalonate, should be the strongest cationic carbon-centered electrophile known up to date.

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Satumov E. T. et al. Protonation and transformations of α-diazo-β-dicarbonyl compounds in superacids: generation of the strongest carbon-centered cationic electrophiles at the protonation of diazomalonates in Friedel–Crafts reactions // Tetrahedron. 2016. Vol. 72. No. 32. pp. 4835-4844.
GOST all authors (up to 50) Copy
Satumov E. T., Medvedev J., Nilov D. I., Sandzhieva M. A., Boyarskaya I. A., Nikolaev N. A., Vasilyev A. V. Protonation and transformations of α-diazo-β-dicarbonyl compounds in superacids: generation of the strongest carbon-centered cationic electrophiles at the protonation of diazomalonates in Friedel–Crafts reactions // Tetrahedron. 2016. Vol. 72. No. 32. pp. 4835-4844.
RIS |
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TY - JOUR
DO - 10.1016/j.tet.2016.06.051
UR - https://doi.org/10.1016%2Fj.tet.2016.06.051
TI - Protonation and transformations of α-diazo-β-dicarbonyl compounds in superacids: generation of the strongest carbon-centered cationic electrophiles at the protonation of diazomalonates in Friedel–Crafts reactions
T2 - Tetrahedron
AU - Satumov, Eugeniy T
AU - Medvedev, Jury
AU - Nilov, Denis I
AU - Sandzhieva, Maria A
AU - Boyarskaya, Irina A
AU - Nikolaev, Nazar A
AU - Vasilyev, Aleksander V
PY - 2016
DA - 2016/08/01 00:00:00
PB - Elsevier
SP - 4835-4844
IS - 32
VL - 72
SN - 0040-4020
SN - 1464-5416
ER -
BibTex |
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@article{2016_Satumov,
author = {Eugeniy T Satumov and Jury Medvedev and Denis I Nilov and Maria A Sandzhieva and Irina A Boyarskaya and Nazar A Nikolaev and Aleksander V Vasilyev},
title = {Protonation and transformations of α-diazo-β-dicarbonyl compounds in superacids: generation of the strongest carbon-centered cationic electrophiles at the protonation of diazomalonates in Friedel–Crafts reactions},
journal = {Tetrahedron},
year = {2016},
volume = {72},
publisher = {Elsevier},
month = {aug},
url = {https://doi.org/10.1016%2Fj.tet.2016.06.051},
number = {32},
pages = {4835--4844},
doi = {10.1016/j.tet.2016.06.051}
}
MLA
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MLA Copy
Satumov, Eugeniy T., et al. “Protonation and transformations of α-diazo-β-dicarbonyl compounds in superacids: generation of the strongest carbon-centered cationic electrophiles at the protonation of diazomalonates in Friedel–Crafts reactions.” Tetrahedron, vol. 72, no. 32, Aug. 2016, pp. 4835-4844. https://doi.org/10.1016%2Fj.tet.2016.06.051.
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