European Journal of Organic Chemistry, volume 2014, issue 14, pages 2993-3000
Thermolysis of 4‐Diazotetrahydrofuran‐3‐ones: Total Change of Reaction Course Compared to Photolysis
Publication type: Journal Article
Publication date: 2014-04-03
Quartile SCImago
Q2
Quartile WOS
Q2
Impact factor: 2.8
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
Thermolysis of 2,2,5,5-tetrasubstituted 4-diazodihydrofuran-3-ones in protic (BnOH) and aprotic (DMSO) media, in contrast to photolysis, gives rise to the formation of 2,2,4,5-substituted 3(2H)-furanones as a result of 1,2-alkyl (aryl) shift. The thermal stability of diazodihydrofuranones in these processes is determined by the nature of the substituents at the C-5 atom of the heterocyclic structure: alkyl and electron-donating groups in the para-position of the aryl substituent notably reduce the persistence of diazodihydrofuranones, whereas aryl groups and electron-withdrawing substituents increase their stability considerably. Thermolysis of substituted 4-diazodihydrofuran-3-ones in DMSO solution is a first-order reaction that furnishes higher yields of furanones than thermolysis in BnOH. The reaction can serve as a preparative method for the synthesis of tetrasubstituted-3(2H)-furanones.
Citations by journals
|
1
2
|
|
|
Journal of Organic Chemistry
|
Journal of Organic Chemistry
2 publications, 28.57%
|
|
Molecules
|
Molecules
1 publication, 14.29%
|
|
Journal of Physical Organic Chemistry
|
Journal of Physical Organic Chemistry
1 publication, 14.29%
|
|
ChemInform
|
ChemInform
1 publication, 14.29%
|
|
Asian Journal of Organic Chemistry
|
Asian Journal of Organic Chemistry
1 publication, 14.29%
|
|
Organic and Biomolecular Chemistry
|
Organic and Biomolecular Chemistry
1 publication, 14.29%
|
|
1
2
|
Citations by publishers
|
1
2
3
|
|
|
Wiley
|
Wiley
3 publications, 42.86%
|
|
American Chemical Society (ACS)
|
American Chemical Society (ACS)
2 publications, 28.57%
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
|
Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 14.29%
|
|
Royal Society of Chemistry (RSC)
|
Royal Society of Chemistry (RSC)
1 publication, 14.29%
|
|
1
2
3
|
- 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":[2015,2016,2017,2018,2019],"ids":[0,0,0,0,0],"codes":[0,0,0,0,0],"imageUrls":["","","","",""],"datasets":[{"label":"Citations number","data":[2,2,1,0,2],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["28.57","28.57","14.29",0,"28.57"],"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":["Journal of Organic Chemistry","Molecules","Journal of Physical Organic Chemistry","ChemInform","Asian Journal of Organic Chemistry","Organic and Biomolecular Chemistry"],"ids":[8697,1770,16036,25372,9409,541],"codes":[0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp"],"datasets":[{"label":"","data":[2,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[28.57,14.29,14.29,14.29,14.29,14.29],"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","American Chemical Society (ACS)","Multidisciplinary Digital Publishing Institute (MDPI)","Royal Society of Chemistry (RSC)"],"ids":[11,40,202,123],"codes":[0,0,0,0],"imageUrls":["\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp"],"datasets":[{"label":"","data":[3,2,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[42.86,28.57,14.29,14.29],"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
Rodina L. L. et al. Thermolysis of 4‐Diazotetrahydrofuran‐3‐ones: Total Change of Reaction Course Compared to Photolysis // European Journal of Organic Chemistry. 2014. Vol. 2014. No. 14. pp. 2993-3000.
GOST all authors (up to 50)
Copy
Rodina L. L., Medvedev J., Galkina O. S., Nikolaev N. A. Thermolysis of 4‐Diazotetrahydrofuran‐3‐ones: Total Change of Reaction Course Compared to Photolysis // European Journal of Organic Chemistry. 2014. Vol. 2014. No. 14. pp. 2993-3000.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/ejoc.201400161
UR - https://doi.org/10.1002%2Fejoc.201400161
TI - Thermolysis of 4‐Diazotetrahydrofuran‐3‐ones: Total Change of Reaction Course Compared to Photolysis
T2 - European Journal of Organic Chemistry
AU - Rodina, Ludmila L.
AU - Medvedev, Jury
AU - Galkina, Olesia S
AU - Nikolaev, Nazar A
PY - 2014
DA - 2014/04/03 00:00:00
PB - Wiley
SP - 2993-3000
IS - 14
VL - 2014
SN - 1434-193X
SN - 1099-0690
ER -
Cite this
BibTex
Copy
@article{2014_Rodina,
author = {Ludmila L. Rodina and Jury Medvedev and Olesia S Galkina and Nazar A Nikolaev},
title = {Thermolysis of 4‐Diazotetrahydrofuran‐3‐ones: Total Change of Reaction Course Compared to Photolysis},
journal = {European Journal of Organic Chemistry},
year = {2014},
volume = {2014},
publisher = {Wiley},
month = {apr},
url = {https://doi.org/10.1002%2Fejoc.201400161},
number = {14},
pages = {2993--3000},
doi = {10.1002/ejoc.201400161}
}
Cite this
MLA
Copy
Rodina, Ludmila L., et al. “Thermolysis of 4‐Diazotetrahydrofuran‐3‐ones: Total Change of Reaction Course Compared to Photolysis.” European Journal of Organic Chemistry, vol. 2014, no. 14, Apr. 2014, pp. 2993-3000. https://doi.org/10.1002%2Fejoc.201400161.