Home / Publications / Retention of a Six-Membered Ring in the Reaction of 2-dialkylaminobenzo[e]-1,3,2-dioxaphosphinin-4-ones with Pentafluorobenzaldehyde: O,N-exchange at Phosphorus

Retention of a Six-Membered Ring in the Reaction of 2-dialkylaminobenzo[e]-1,3,2-dioxaphosphinin-4-ones with Pentafluorobenzaldehyde: O,N-exchange at Phosphorus

Vladimir Fedorovich Mironov
Liliya Mullachmetovna Burnaeva 2
Liliya Mullachmetovna Burnaeva
Gulnara Askarovna Ivkova 2
Gulnara Askarovna Ivkova
Alexey Borisovich Dobrynin 1
Alexey Borisovich Dobrynin
Ekaterina Vladimirovna Mironova 1
Ekaterina Vladimirovna Mironova
Igor Anatol'evich Litvinov 1
Igor Anatol'evich Litvinov
Published 2013-05-08
CommunicationVolume 23, Issue 3, 171-173
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Mironov V. F. et al. Retention of a Six-Membered Ring in the Reaction of 2-dialkylaminobenzo[e]-1,3,2-dioxaphosphinin-4-ones with Pentafluorobenzaldehyde: O,N-exchange at Phosphorus // Mendeleev Communications. 2013. Vol. 23. No. 3. pp. 171-173.
GOST all authors (up to 50) Copy
Mironov V. F., Burnaeva L. M., Ivkova G. A., Dobrynin A. B., Mironova E. V., Litvinov I. A. Retention of a Six-Membered Ring in the Reaction of 2-dialkylaminobenzo[e]-1,3,2-dioxaphosphinin-4-ones with Pentafluorobenzaldehyde: O,N-exchange at Phosphorus // Mendeleev Communications. 2013. Vol. 23. No. 3. pp. 171-173.
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TY - JOUR
DO - 10.1016/j.mencom.2013.05.018
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.05.018
TI - Retention of a Six-Membered Ring in the Reaction of 2-dialkylaminobenzo[e]-1,3,2-dioxaphosphinin-4-ones with Pentafluorobenzaldehyde: O,N-exchange at Phosphorus
T2 - Mendeleev Communications
AU - Mironov, Vladimir Fedorovich
AU - Burnaeva, Liliya Mullachmetovna
AU - Ivkova, Gulnara Askarovna
AU - Dobrynin, Alexey Borisovich
AU - Mironova, Ekaterina Vladimirovna
AU - Litvinov, Igor Anatol'evich
PY - 2013
DA - 2013/05/08
PB - Mendeleev Communications
SP - 171-173
IS - 3
VL - 23
ER -
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@article{2013_Mironov,
author = {Vladimir Fedorovich Mironov and Liliya Mullachmetovna Burnaeva and Gulnara Askarovna Ivkova and Alexey Borisovich Dobrynin and Ekaterina Vladimirovna Mironova and Igor Anatol'evich Litvinov},
title = {Retention of a Six-Membered Ring in the Reaction of 2-dialkylaminobenzo[e]-1,3,2-dioxaphosphinin-4-ones with Pentafluorobenzaldehyde: O,N-exchange at Phosphorus},
journal = {Mendeleev Communications},
year = {2013},
volume = {23},
publisher = {Mendeleev Communications},
month = {May},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.05.018},
number = {3},
pages = {171--173},
doi = {10.1016/j.mencom.2013.05.018}
}
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Mironov, Vladimir Fedorovich, et al. “Retention of a Six-Membered Ring in the Reaction of 2-dialkylaminobenzo[e]-1,3,2-dioxaphosphinin-4-ones with Pentafluorobenzaldehyde: O,N-exchange at Phosphorus.” Mendeleev Communications, vol. 23, no. 3, May. 2013, pp. 171-173. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.05.018.

Abstract

The title reaction leads to the formation of diastereoisomeric 2-[(dialkylamino)(pentafluorophenyl)methyl]benzo[e]-1,3,2-dioxaphosphinine-2,4-diones in a ratio of 70 : 30. The configuration of chiral centres for the preferable diastereoisomer was determined by single crystal X-ray diffraction analysis.

References

1.
V. F. Mironov, I. A. Litvinov, A. T. Gubaidullin, R. M. Aminova, L. M. Burnaeva, N. M. Azancheev, M. E. Filatov and I. V. Konovalova, Russ. J. Gen. Chem., 1998, 68, 1027 (Zh. Obshch. Khim., 1998, 68, 1080).
2.
Mironov V.F., Ivkova G.A., Abdrakhmanova L.M., Mironova E.V., Krivolapov D.B., Konovalova I.V.
Mendeleev Communications, 2011
3.
V. F. Mironov, L. M. Burnaeva, A. T. Gubaidullin, I. A. Brazhnikova, I. A. Litvinov, S. V. Romanov and I. V. Konovalova, Russ. J. Gen. Chem., 2000, 70, 1539 (Zh. Obshch. Khim., 2000, 70, 1637).
5.
V. F. Mironov, A. T. Gubaidullin, L. M. Burnaeva, I. A. Litvinov, G. A. Ivkova, S. V. Romanov, T. A. Zyablikova, A. I. Konovalov and I. V. Konovalova, Russ. J. Gen. Chem., 2004, 74, 32 (Zh. Obshch. Khim., 2004, 74, 39).
6.
Yu. Yu. Kotorova, A. T. Gubaidullin, V. F. Mironov, L. M. Burnaeva, A. B. Dobrynin, R. Z. Musin, I. A. Litvinov and I. V. Konovalova, Russ. J. Gen. Chem., 2006, 76, 437 (Zh. Obshch. Khim., 2006, 76, 459).
7.
L. M. Burnaeva, V. F. Mironov, Yu. Yu. Borisova, A. T. Gubaidullin, A. B. Dobrynin, I. A. Litvinov, G. A. Ivkova, N. K. Amerkhanova and I.V. Konovalova, Russ. J. Gen. Chem., 2008, 78, 410 (Zh. Obshch. Khim., 2008, 78, 425).
8.
G. M. Karp, J. Org. Chem., 1999, 64, 8156.
9.
V. F. Mironov, I. A. Litvinov, A. T. Gubaidullin, I. V. Konovalova, T. A. Zyablikova, L. M. Burnaeva, S. V. Romanov and R. A. Mavleev, Russ. J. Gen. Chem., 2000, 70, 1706 (Zh. Obshch. Khim., 2000, 70, 1812).
10.
V. F. Mironov, L. M. Burnaeva, I. V. Konovalova, G. A. Khlopushina, R. A. Mavleev and P. P. Chernov, Zh. Obshch. Khim., 1993, 63, 25 (in Russian).
11.
V. P. Evdakov, L. I. Mizrakh and L. Yu. Sandalova, Dokl. Akad. Nauk SSSR, 1965, 162, 573 (in Russian).
12.
L. Yu. Sandalova, L. I. Mizrakh and V. P. Evdakov, Zh. Obshch. Khim., 1965, 35, 1314 (in Russian).
13.
Reactions of tervalent phosphorus–nitrogen compounds. Part II. Aldehydes and ketones
Hudson R.F., Searle R.J., Devitt F.H.
Journal of the Chemical Society B Physical Organic, 1966
14.
Reactions of aminophosphines with α,β-unsaturated aldehydes
Pudovik A.N., Batyeva �.S.
Russian Chemical Bulletin, 1968
15.
R. S. Burgada and J. Roussel, Bull. Soc. Chim. Fr., 1970, 192.
16.
K. C. Kumara Swamy, S. Kumaraswamy, K. S. Kumar and C. Muthiah, Tetrahedron Lett., 2005, 46, 3347.
17.
A short history of SHELX
Sheldrick G.M.
Acta Crystallographica Section A Foundations of Crystallography, 2007
18.
E-map improvement in direct procedures
Altomare A., Cascarano G., Giacovazzo C., Viterbo D.
Acta Crystallographica Section A Foundations of Crystallography, 1991
19.
G. M. Sheldrick, SHELX-97. Programs for Crystal Structure Analysis (Release 97-2), University of Göttingen, 1997.
20.
WinGXsuite for small-molecule single-crystal crystallography
Farrugia L.J.
Journal of Applied Crystallography, 1999
21.
APEX2 (Version 2.1), SAINTPlus. Data Reduction and Correction Program (Version 7.31A), Bruker Advanced X-ray Solutions, Bruker AXS Inc., Madison, Wisconsin, USA, 2006.
22.
Structure of dioxo[2‐(salicylidenamino)phenolato(2‐)‐O,N,O'][tris(dimethylamino)phosphine oxide]tungsten(VI)
Spek A.L., Terheijden J., Kraaykamp J.G., Timmer K.
Acta Crystallographica Section C Crystal Structure Communications, 1990