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Effective one-pot synthesis of 2,3-dialkyl-1,4-dicyclopropyl-butane-1,4-diones catalyzed by Cp2TiCl2

Leila Osmanovna Khafizova 1
Leila Osmanovna Khafizova
, 
Mariya Gennad'evna Shaibakova 1
Mariya Gennad'evna Shaibakova
, 
Nuri Mamedeevich Chobanov 1
Nuri Mamedeevich Chobanov
, 
Tat'yana Viktorovna Tyumkina 1
Tat'yana Viktorovna Tyumkina
,  , 
Nataliya Romanovna Porod'ko 1
Nataliya Romanovna Porod'ko
, 
10.1016/j.mencom.2016.04.015
Published 2016-04-28
Communication , Volume 26, Issue 3, 223-225
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Khafizova L. O. et al. Effective one-pot synthesis of 2,3-dialkyl-1,4-dicyclopropyl-butane-1,4-diones catalyzed by Cp2TiCl2 // Mendeleev Communications. 2016. Vol. 26. No. 3. pp. 223-225.
GOST all authors (up to 50) Copy
Khafizova L. O., Shaibakova M. G., Chobanov N. M., Tyumkina T. V., Gubaidullin R. R., Porod'ko N. R., Dzhemilev U. M. Effective one-pot synthesis of 2,3-dialkyl-1,4-dicyclopropyl-butane-1,4-diones catalyzed by Cp2TiCl2 // Mendeleev Communications. 2016. Vol. 26. No. 3. pp. 223-225.
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TY - JOUR
DO - 10.1016/j.mencom.2016.04.015
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.04.015
TI - Effective one-pot synthesis of 2,3-dialkyl-1,4-dicyclopropyl-butane-1,4-diones catalyzed by Cp2TiCl2
T2 - Mendeleev Communications
AU - Khafizova, Leila Osmanovna
AU - Shaibakova, Mariya Gennad'evna
AU - Chobanov, Nuri Mamedeevich
AU - Tyumkina, Tat'yana Viktorovna
AU - Gubaidullin, Rinat Ravil'evich
AU - Porod'ko, Nataliya Romanovna
AU - Dzhemilev, Usein Memetovich
PY - 2016
DA - 2016/04/28
PB - Mendeleev Communications
SP - 223-225
IS - 3
VL - 26
ER -
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@article{2016_Khafizova,
author = {Leila Osmanovna Khafizova and Mariya Gennad'evna Shaibakova and Nuri Mamedeevich Chobanov and Tat'yana Viktorovna Tyumkina and Rinat Ravil'evich Gubaidullin and Nataliya Romanovna Porod'ko and Usein Memetovich Dzhemilev},
title = {Effective one-pot synthesis of 2,3-dialkyl-1,4-dicyclopropyl-butane-1,4-diones catalyzed by Cp2TiCl2},
journal = {Mendeleev Communications},
year = {2016},
volume = {26},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.04.015},
number = {3},
pages = {223--225},
doi = {10.1016/j.mencom.2016.04.015}
}
MLA
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MLA Copy
Khafizova, Leila Osmanovna, et al. “Effective one-pot synthesis of 2,3-dialkyl-1,4-dicyclopropyl-butane-1,4-diones catalyzed by Cp2TiCl2.” Mendeleev Communications, vol. 26, no. 3, Apr. 2016, pp. 223-225. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.04.015.

Abstract

2,3-Dialkyl-l,4-dicyclopropylbutane-1,4-diones were prepared in one pot from symmetrical acetylenes, ethylaluminum dichloride and methyl cyclopropanecarboxylate in the presence of magnesium metal and Cp2TiCl2 (10 mol%) as a catalyst in 62–66% yield. Comparison of 1,4-dicyclopropylbutane-1,4-diones with other analogues to form furans in the course of the Paal–Knorr reaction was made by quantum chemical DFT calculations.

References

2.
Synthesis of Jasmonoids, a Review
Ho T.
Synthetic Communications, 1974
3.
New route to .gamma.-ketoaldehydes. Application to the synthesis of cis-jasmone
Oshima K., Yamamoto H., Nozaki H.
Journal of the American Chemical Society, 1973
4.
10.1016/j.mencom.2016.04.015_sbref0005d
Stetter
Org. React., 1991
6.
A Convenient Synthesis of 1,4-Diketones
Motoyoshiya J., Hongo Y., Tanaka H., Hayashi S.
Synthetic Communications, 1991
8.
10.1016/j.mencom.2016.04.015_sbref0015a
Hassner
1991
11.
10.1016/j.mencom.2016.04.015_sbref0020b
O’Neill
1991
14.
Homogeneous gold-catalyzed efficient oxidative dimerization of propargylic acetates.
Cui L., Zhang G., Zhang L.
Bioorganic and Medicinal Chemistry Letters, 2009
15.
A Synthesis of cis-Jasmone
Stork G., Borch R.
Journal of the American Chemical Society, 1964
16.
An Efficient Synthesis of cis-Jasmone
Büchi G., Wüest H.
Journal of Organic Chemistry, 1966
17.
Synthesis of ketols of the natural pyrethrins
Crombie L., Hemesley P., Pattenden G.
Journal of the Chemical Society C Organic, 1969
19.
A ready route to cis-jasmone via 1,3-dithian-derived 1,4-diketones
Ellison R.A., Woessner W.D.
Journal of the Chemical Society Chemical Communications, 1972
20.
The efficient one-pot synthesis of tetraalkyl substituted furans from symmetrical acetylenes, EtAlCl2, and carboxylic esters catalyzed by Cp2TiCl2
Shaibakova M.G., Khafizova L.O., Chobanov N.M., Gubaidullin R.R., Popod’ko N.R., Dzhemilev U.M.
Tetrahedron Letters, 2014
21.
Synthesis of tetrasubstituted furans by multicomponent reaction of alkynes with dichloro(ethyl)aluminum and carboxylic acid esters in the presence of Cp2TiCl2
Khafizova L.O., Shaibakova M.G., Chobanov N.M., Gubaidullin R.R., Tyumkina T.V., Dzhemilev U.M.
Russian Journal of Organic Chemistry, 2015
22.
L. O. Khafizova, M.G. Shaibakova, T.V. Tyumkina, N.M. Chobanov and U. M. Dzhemilev, Patent RF 2565789 C1, 08.04.2014.
23.
Stereoisomer effects on the Paal-Knorr synthesis of pyrroles
Szakal-Quin G., Graham D.G., Millington D.S., Maltby D.A., McPhail A.T.
Journal of Organic Chemistry, 1986
25.
Synthese von Furfuranderivaten aus dem Diacetbernsteinsäureester
Knorr L.
Berichte der deutschen chemischen Gesellschaft, 1884
27.
Pyridoxamine:  An Extremely Potent Scavenger of 1,4-Dicarbonyls
Amarnath V., Amarnath K., Amarnath K., Davies S., Roberts L.J.
Chemical Research in Toxicology, 2004
28.
Intermediates in the Paal-Knorr synthesis of pyrroles
Amarnath V., Anthony D.C., Amarnath K., Valentine W.M., Wetterau L.A., Graham D.G.
Journal of Organic Chemistry, 1991
29.
Intermediates in the Paal-Knorr Synthesis of Furans
Amarnath V., Amarnath K.
Journal of Organic Chemistry, 1995
34.
Generalized Gradient Approximation Made Simple
Perdew J.P., Burke K., Ernzerhof M.
Physical Review Letters, 1996
35.
G. A. Zhurko and D. A. Zhurko, ChemCraft 1.6, 2009.
36.
Rates of solvolysis of 2-cyclopropylethyl brosylates
Dewar M.J., Harris J.M.
Journal of the American Chemical Society, 1968
37.
Secondary hydrogen isotope effects—IX
Nikoletić M., Borçić S., Sunko D.E.
Tetrahedron, 1967
38.
Scope, limitations, and mechanism of the homoconjugate electrophilic addition of hydrogen halides
Lambert J.B., Napoli J.J., Johnson K.K., Taba K.N.
Journal of Organic Chemistry, 1985
39.
Strategic Application and Transformation of ortho-Disubstituted Phenyl and Cyclopropyl Ketones To Expand the Scope of Hydrogen Borrowing Catalysis
Frost J.R., Cheong C.B., Akhtar W.M., Caputo D.F., Stevenson N.G., Donohoe T.J.
Journal of the American Chemical Society, 2015
40.
Dimeric carbamoylguanidine-type histamine H2 receptor ligands: A new class of potent and selective agonists
Kagermeier N., Werner K., Keller M., Baumeister P., Bernhardt G., Seifert R., Buschauer A.
Bioorganic and Medicinal Chemistry, 2015