Synthesis of 1,2,3,4,5-Penta(methoxycarbonyl)cyclopentadienides through Electrocyclic Ring Closure and Ring Contraction Reactions
Rinat F Salikov
1
,
Konstantin P Trainov
1
,
Dmitry Platonov
2
,
Dmitry N Platonov
1
,
Alexander Yu Belyy
1
,
Publication type: Journal Article
Publication date: 2018-08-07
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
The mechanism for the reaction of dimethyl malonate with dimethyl acetylenedicarboxylate in the presence of pyridine and acetic acid to form isomeric octa(methoxycarbonyl)cycloheptadienes was established. The formation of intermediary N‐[di(methoxycarbonyl)vinyl]pyridinium acetate was proven by means of NMR spectroscopy. On the basis of the established mechanism, dimethyl dibromosuccinate was proposed to be used instead of dimethyl acetylenedicarboxylate. A novel method for the synthesis of penta(methoxycarbonyl)cyclopentadienylsodium through the reduction of hepta(methoxycarbonyl)cycloheptatriene with sodium borohydride, electrocyclic ring contraction and retro‐[2+2]‐cycloaddition was developed.
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GOST
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Salikov R. F. et al. Synthesis of 1,2,3,4,5-Penta(methoxycarbonyl)cyclopentadienides through Electrocyclic Ring Closure and Ring Contraction Reactions // European Journal of Organic Chemistry. 2018. Vol. 2018. No. 36. pp. 5065-5068.
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Salikov R. F., Trainov K. P., Platonov D., Platonov D. N., Belyy A. Yu., Tomilov Y. V. Synthesis of 1,2,3,4,5-Penta(methoxycarbonyl)cyclopentadienides through Electrocyclic Ring Closure and Ring Contraction Reactions // European Journal of Organic Chemistry. 2018. Vol. 2018. No. 36. pp. 5065-5068.
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RIS
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TY - JOUR
DO - 10.1002/ejoc.201800732
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201800732
TI - Synthesis of 1,2,3,4,5-Penta(methoxycarbonyl)cyclopentadienides through Electrocyclic Ring Closure and Ring Contraction Reactions
T2 - European Journal of Organic Chemistry
AU - Salikov, Rinat F
AU - Trainov, Konstantin P
AU - Platonov, Dmitry
AU - Platonov, Dmitry N
AU - Belyy, Alexander Yu
AU - Tomilov, Yury V.
PY - 2018
DA - 2018/08/07
PB - Wiley
SP - 5065-5068
IS - 36
VL - 2018
SN - 1434-193X
SN - 1099-0690
ER -
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BibTex (up to 50 authors)
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@article{2018_Salikov,
author = {Rinat F Salikov and Konstantin P Trainov and Dmitry Platonov and Dmitry N Platonov and Alexander Yu Belyy and Yury V. Tomilov},
title = {Synthesis of 1,2,3,4,5-Penta(methoxycarbonyl)cyclopentadienides through Electrocyclic Ring Closure and Ring Contraction Reactions},
journal = {European Journal of Organic Chemistry},
year = {2018},
volume = {2018},
publisher = {Wiley},
month = {aug},
url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201800732},
number = {36},
pages = {5065--5068},
doi = {10.1002/ejoc.201800732}
}
Cite this
MLA
Copy
Salikov, Rinat F., et al. “Synthesis of 1,2,3,4,5-Penta(methoxycarbonyl)cyclopentadienides through Electrocyclic Ring Closure and Ring Contraction Reactions.” European Journal of Organic Chemistry, vol. 2018, no. 36, Aug. 2018, pp. 5065-5068. https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201800732.
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