Home / Publications / One-pot cascade assembling of 3-substituted tetracyanocyclopropanes from alkylidenemalononitriles and malononitrile by the only bromine direct action

One-pot cascade assembling of 3-substituted tetracyanocyclopropanes from alkylidenemalononitriles and malononitrile by the only bromine direct action

Anatoly Nikolaevich Vereshchagin 1
Anatoly Nikolaevich Vereshchagin
Nikita Olegovich Stepanov 1
Nikita Olegovich Stepanov
Gennady Ivanovich Nikishin 1
Gennady Ivanovich Nikishin
Published 2009-11-02
CommunicationVolume 19, Issue 6, 324-325
33
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Vereshchagin A. N. et al. One-pot cascade assembling of 3-substituted tetracyanocyclopropanes from alkylidenemalononitriles and malononitrile by the only bromine direct action // Mendeleev Communications. 2009. Vol. 19. No. 6. pp. 324-325.
GOST all authors (up to 50) Copy
Vereshchagin A. N., Elinson M. N., Stepanov N. O., Nikishin G. I. One-pot cascade assembling of 3-substituted tetracyanocyclopropanes from alkylidenemalononitriles and malononitrile by the only bromine direct action // Mendeleev Communications. 2009. Vol. 19. No. 6. pp. 324-325.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2009.11.010
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2009.11.010
TI - One-pot cascade assembling of 3-substituted tetracyanocyclopropanes from alkylidenemalononitriles and malononitrile by the only bromine direct action
T2 - Mendeleev Communications
AU - Vereshchagin, Anatoly Nikolaevich
AU - Elinson, Michail Nikolaevich
AU - Stepanov, Nikita Olegovich
AU - Nikishin, Gennady Ivanovich
PY - 2009
DA - 2009/11/02
PB - Mendeleev Communications
SP - 324-325
IS - 6
VL - 19
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2009_Vereshchagin,
author = {Anatoly Nikolaevich Vereshchagin and Michail Nikolaevich Elinson and Nikita Olegovich Stepanov and Gennady Ivanovich Nikishin},
title = {One-pot cascade assembling of 3-substituted tetracyanocyclopropanes from alkylidenemalononitriles and malononitrile by the only bromine direct action},
journal = {Mendeleev Communications},
year = {2009},
volume = {19},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2009.11.010},
number = {6},
pages = {324--325},
doi = {10.1016/j.mencom.2009.11.010}
}
MLA
Cite this
MLA Copy
Vereshchagin, Anatoly Nikolaevich, et al. “One-pot cascade assembling of 3-substituted tetracyanocyclopropanes from alkylidenemalononitriles and malononitrile by the only bromine direct action.” Mendeleev Communications, vol. 19, no. 6, Nov. 2009, pp. 324-325. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2009.11.010.

Abstract

The new cascade reaction was found: the formation of cyclopropanes from alkylidenemalononitriles and malononitrile by the only bromine direct action; the action of aqueous bromine on the equal amounts of alkylidenemalononitriles and malononitrile in EtOH–H2O solutions results in the formation of 3-substituted 1,1,2,2-tetracyanocyclopropanes in 55–98% yields.

References

1.
10.1016/j.mencom.2009.11.010_bib1
Rappoport
The Chemistry of the Cyclopropyl Group, 1996
2.
Asymmetric Total Synthesis of Halicholactone
Baba Y., Saha G., Nakao S., Iwata C., Tanaka T., Ibuka T., Ohishi H., Takemoto Y.
Journal of Organic Chemistry, 2000
4.
Fluorinated phenylcyclopropylamines. Part 3: Inhibition of monoamine oxidase A and B
Yoshida S., Rosen T.C., Meyer O.G., Sloan M.J., Ye S., Haufe G., Kirk K.L.
Bioorganic and Medicinal Chemistry, 2004
7.
H. Lebel, J. F. Marcoux, C. Molinaro and A. B. Charette, Chem. Rev., 2003, 1015.
8.
G. Bonavent, M. Causse, M. Guitard and R. Fraisse-Julien, Bull. Soc. Chim. Fr., 1964, 2462.
9.
A New Synthesis of Tetracyanocyclopropanes
Hart H., Kim Y.C.
Journal of Organic Chemistry, 1966
11.
Neue planare π-Systeme
Hopf H., Kreutzer M.
Angewandte Chemie, 1990
12.
10.1016/j.mencom.2009.11.010_bib9
Nasakin
Zh. Org. Khim., 1993
13.
10.1016/j.mencom.2009.11.010_bib10
Kayukova
Zh. Org. Khim., 2006
14.
Rates of Ionization of Pseudo Acids.1 IV. Relation between Rates and Equilibria
Pearson R.G., Dillon R.L.
Journal of the American Chemical Society, 1953