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
,
Medvedev Jury
1
,
Nilov Denis I
1
,
Sandzhieva Maria A
2, 3, 4
,
Boyarskaya Irina A
1
,
Nikolaev Nazar A
1
,
Vasilyev Aleksander V
2, 3, 4
2
Department of Organic Chemistry, Institute of Chemistry
4
Universitetskaya nab. 7/9 Saint Petersburg 199034 Russia
|
Publication type: Journal Article
Publication date: 2016-08-01
Journal:
Tetrahedron
Quartile SCImago
Q2
Quartile WOS
Q3
Impact factor: 2.1
ISSN: 00404020, 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.
Citations by journals
|
1
2
|
|
|
Tetrahedron Letters
|
Tetrahedron Letters
2 publications, 12.5%
|
|
Organic Reaction Mechanisms
|
Organic Reaction Mechanisms
2 publications, 12.5%
|
|
Journal of Physical Organic Chemistry
|
Journal of Physical Organic Chemistry
1 publication, 6.25%
|
|
Russian Chemical Reviews
|
Russian Chemical Reviews
1 publication, 6.25%
|
|
ChemInform
|
ChemInform
1 publication, 6.25%
|
|
Angewandte Chemie - International Edition
|
Angewandte Chemie - International Edition
1 publication, 6.25%
|
|
Angewandte Chemie
|
Angewandte Chemie
1 publication, 6.25%
|
|
Advanced Synthesis and Catalysis
|
Advanced Synthesis and Catalysis
1 publication, 6.25%
|
|
Organic Letters
|
Organic Letters
1 publication, 6.25%
|
|
Journal of Physical Chemistry C
|
Journal of Physical Chemistry C
1 publication, 6.25%
|
|
New Journal of Chemistry
|
New Journal of Chemistry
1 publication, 6.25%
|
|
Organic and Biomolecular Chemistry
|
Organic and Biomolecular Chemistry
1 publication, 6.25%
|
|
Russian Journal of Organic Chemistry
|
Russian Journal of Organic Chemistry
1 publication, 6.25%
|
|
Synthesis
|
Synthesis
1 publication, 6.25%
|
|
1
2
|
Citations by publishers
|
1
2
3
4
5
6
7
|
|
|
Wiley
|
Wiley
7 publications, 43.75%
|
|
Elsevier
|
Elsevier
2 publications, 12.5%
|
|
American Chemical Society (ACS)
|
American Chemical Society (ACS)
2 publications, 12.5%
|
|
Royal Society of Chemistry (RSC)
|
Royal Society of Chemistry (RSC)
2 publications, 12.5%
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 6.25%
|
|
Pleiades Publishing
|
Pleiades Publishing
1 publication, 6.25%
|
|
Thieme
|
Thieme
1 publication, 6.25%
|
|
1
2
3
4
5
6
7
|
- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2016,2017,2018,2019,2020,2021,2022],"ids":[0,0,0,0,0,0,0],"codes":[0,0,0,0,0,0,0],"imageUrls":["","","","","","",""],"datasets":[{"label":"Citations number","data":[3,4,2,3,3,0,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["18.75","25","12.5","18.75","18.75",0,"6.25"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["Tetrahedron Letters","Organic Reaction Mechanisms","Journal of Physical Organic Chemistry","Russian Chemical Reviews","ChemInform","Angewandte Chemie - International Edition","Angewandte Chemie","Advanced Synthesis and Catalysis","Organic Letters","Journal of Physical Chemistry C","New Journal of Chemistry","Organic and Biomolecular Chemistry","Russian Journal of Organic Chemistry","Synthesis"],"ids":[6133,42256,16036,23802,25372,19215,25450,3906,3315,8859,1404,541,5728,10934],"codes":[0,0,0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/oZgeErrVFhuDksyqFURLvYS1wtVSBWczh001igGo_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp"],"datasets":[{"label":"","data":[2,2,1,1,1,1,1,1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[12.5,12.5,6.25,6.25,6.25,6.25,6.25,6.25,6.25,6.25,6.25,6.25,6.25,6.25],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["Wiley","Elsevier","American Chemical Society (ACS)","Royal Society of Chemistry (RSC)","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii","Pleiades Publishing","Thieme"],"ids":[11,17,40,123,9422,101,135],"codes":[0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp","\/storage\/images\/resized\/oZgeErrVFhuDksyqFURLvYS1wtVSBWczh001igGo_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp"],"datasets":[{"label":"","data":[7,2,2,2,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[43.75,12.5,12.5,12.5,6.25,6.25,6.25],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}
Metrics
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
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.
Cite this
RIS
Copy
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 -
Cite this
BibTex
Copy
@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}
}
Cite this
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.