Home / Publications / Unexpected formation of 4-arylcyclopentane-1,1,3,3-tetracarboxylates in GaCl3-catalyzed reaction of 2-arylcyclopropane-1,1-dicarboxylates with tetrasubstituted 1-pyrazolines

Unexpected formation of 4-arylcyclopentane-1,1,3,3-tetracarboxylates in GaCl3-catalyzed reaction of 2-arylcyclopropane-1,1-dicarboxylates with tetrasubstituted 1-pyrazolines

Roman Aleksandrovich Novikov 1
Roman Aleksandrovich Novikov
,  , 
Oleg Matveevich Nefedov 1
Oleg Matveevich Nefedov
10.1016/j.mencom.2012.06.002
Published 2012-06-13
Communication , Volume 22, Issue 4, 181-183
11
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Novikov R. A., Tomilov Y. V., Nefedov O. M. Unexpected formation of 4-arylcyclopentane-1,1,3,3-tetracarboxylates in GaCl3-catalyzed reaction of 2-arylcyclopropane-1,1-dicarboxylates with tetrasubstituted 1-pyrazolines // Mendeleev Communications. 2012. Vol. 22. No. 4. pp. 181-183.
GOST all authors (up to 50) Copy
Novikov R. A., Tomilov Y. V., Nefedov O. M. Unexpected formation of 4-arylcyclopentane-1,1,3,3-tetracarboxylates in GaCl3-catalyzed reaction of 2-arylcyclopropane-1,1-dicarboxylates with tetrasubstituted 1-pyrazolines // Mendeleev Communications. 2012. Vol. 22. No. 4. pp. 181-183.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2012.06.002
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.06.002
TI - Unexpected formation of 4-arylcyclopentane-1,1,3,3-tetracarboxylates in GaCl3-catalyzed reaction of 2-arylcyclopropane-1,1-dicarboxylates with tetrasubstituted 1-pyrazolines
T2 - Mendeleev Communications
AU - Novikov, Roman Aleksandrovich
AU - Tomilov, Yury Vasil'evich
AU - Nefedov, Oleg Matveevich
PY - 2012
DA - 2012/06/13
PB - Mendeleev Communications
SP - 181-183
IS - 4
VL - 22
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2012_Novikov,
author = {Roman Aleksandrovich Novikov and Yury Vasil'evich Tomilov and Oleg Matveevich Nefedov},
title = {Unexpected formation of 4-arylcyclopentane-1,1,3,3-tetracarboxylates in GaCl3-catalyzed reaction of 2-arylcyclopropane-1,1-dicarboxylates with tetrasubstituted 1-pyrazolines},
journal = {Mendeleev Communications},
year = {2012},
volume = {22},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.06.002},
number = {4},
pages = {181--183},
doi = {10.1016/j.mencom.2012.06.002}
}
MLA
Cite this
MLA Copy
Novikov, Roman Aleksandrovich, et al. “Unexpected formation of 4-arylcyclopentane-1,1,3,3-tetracarboxylates in GaCl3-catalyzed reaction of 2-arylcyclopropane-1,1-dicarboxylates with tetrasubstituted 1-pyrazolines.” Mendeleev Communications, vol. 22, no. 4, Jun. 2012, pp. 181-183. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.06.002.

Abstract

Gallium trichloride-catalyzed reaction between 2-arylcyclopropane-1,1-dicarboxylates and 3,3,5,5-tetrasubstituted 1-pyrazolines affords 4-arylcyclopentane-1,1,3,3-tetracarboxylates, which originate from cycloaddition of the two molecules of the starting cyclopropane with the loss of one arylidene fragment subtracted by the 1-pyrazoline.

References

3.
Mel’nikov M.Y., Budynina E.M., Ivanova O.A., Trushkov I.V.
Mendeleev Communications, 2011
5.
[3+2] Cyclodimerization of 2-arylcyclopropane-1,1-diesters. Lewis acid induced reversion of cyclopropane umpolung
Chagarovskiy A.O., Ivanova O.A., Budynina E.M., Trushkov I.V., Melnikov M.Y.
Tetrahedron Letters, 2011
6.
(3 + 3)-Cyclodimerization of Donor–Acceptor Cyclopropanes. Three Routes to Six-Membered Rings
Ivanova O.A., Budynina E.M., Chagarovskiy A.O., Trushkov I.V., Melnikov M.Y.
Journal of Organic Chemistry, 2011
7.
Domino Cyclodimerization of Indole-Derived Donor-Acceptor Cyclopropanes: One-Step Construction of the Pentaleno[1,6-a,b]indole Skeleton
Ivanova O.A., Budynina E.M., Chagarovskiy A.O., Rakhmankulov E.R., Trushkov I.V., Semeykin A.V., Shimanovskii N.L., Melnikov M.Y.
Chemistry - A European Journal, 2011
8.
Reactions of diazo esters with electron-deficient alkenes in the presence of Lewis acids
Novikov R.A., Platonov D.N., Dokichev V.A., Tomilov Y.V., Nefedov O.M.
Russian Chemical Bulletin, 2010
11.
10.1016/j.mencom.2012.06.002_bib0035_3
de Simone
Synthesis, 2009