Home / Publications / Formation of (1,2-dihydroxynaphth-4-yl)[tris(diethylamino)]-phosphonium bromides in the reaction of 1,2-naphthoquinones with tris(diethylamino)phosphine

Formation of (1,2-dihydroxynaphth-4-yl)[tris(diethylamino)]-phosphonium bromides in the reaction of 1,2-naphthoquinones with tris(diethylamino)phosphine

Andrey Vladimirovich Bogdanov 1
Andrey Vladimirovich Bogdanov
,  , 
Nadezhda R Khasiyatullina 1
Nadezhda R Khasiyatullina
, 
Dmitry Borisovich Krivolapov 1
Dmitry Borisovich Krivolapov
, 
Igor Anatol'evich Litvinov 1
Igor Anatol'evich Litvinov
, 
Aleksandr Ivanovich Konovalov 1
Aleksandr Ivanovich Konovalov
10.1016/j.mencom.2007.05.018
Published 2007-05-03
Communication , Volume 17, Issue 3, 183-185
7
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Bogdanov A. V. et al. Formation of (1,2-dihydroxynaphth-4-yl)[tris(diethylamino)]-phosphonium bromides in the reaction of 1,2-naphthoquinones with tris(diethylamino)phosphine // Mendeleev Communications. 2007. Vol. 17. No. 3. pp. 183-185.
GOST all authors (up to 50) Copy
Bogdanov A. V., Mironov V. F., Khasiyatullina N. R., Krivolapov D. B., Litvinov I. A., Konovalov A. I. Formation of (1,2-dihydroxynaphth-4-yl)[tris(diethylamino)]-phosphonium bromides in the reaction of 1,2-naphthoquinones with tris(diethylamino)phosphine // Mendeleev Communications. 2007. Vol. 17. No. 3. pp. 183-185.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2007.05.018
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2007.05.018
TI - Formation of (1,2-dihydroxynaphth-4-yl)[tris(diethylamino)]-phosphonium bromides in the reaction of 1,2-naphthoquinones with tris(diethylamino)phosphine
T2 - Mendeleev Communications
AU - Bogdanov, Andrey Vladimirovich
AU - Mironov, Vladimir Fedorovich
AU - Khasiyatullina, Nadezhda R
AU - Krivolapov, Dmitry Borisovich
AU - Litvinov, Igor Anatol'evich
AU - Konovalov, Aleksandr Ivanovich
PY - 2007
DA - 2007/05/03
PB - Mendeleev Communications
SP - 183-185
IS - 3
VL - 17
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2007_Bogdanov,
author = {Andrey Vladimirovich Bogdanov and Vladimir Fedorovich Mironov and Nadezhda R Khasiyatullina and Dmitry Borisovich Krivolapov and Igor Anatol'evich Litvinov and Aleksandr Ivanovich Konovalov},
title = {Formation of (1,2-dihydroxynaphth-4-yl)[tris(diethylamino)]-phosphonium bromides in the reaction of 1,2-naphthoquinones with tris(diethylamino)phosphine},
journal = {Mendeleev Communications},
year = {2007},
volume = {17},
publisher = {Mendeleev Communications},
month = {May},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2007.05.018},
number = {3},
pages = {183--185},
doi = {10.1016/j.mencom.2007.05.018}
}
MLA
Cite this
MLA Copy
Bogdanov, Andrey Vladimirovich, et al. “Formation of (1,2-dihydroxynaphth-4-yl)[tris(diethylamino)]-phosphonium bromides in the reaction of 1,2-naphthoquinones with tris(diethylamino)phosphine.” Mendeleev Communications, vol. 17, no. 3, May. 2007, pp. 183-185. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2007.05.018.

Abstract

The title reaction leads to the formation of betaines containing a phosphorus–carbon bond, 2-hydroxy-4-[tris(diethylamino)-phosphonium]naphthyl-1-ates, which react with bromine and moist acetone (or hydrogen bromide), as well as diethylammonium chloride, to give (1,2-dihydroxynaphth-4-yl)[tris(diethylamino)]phosphonium bromide derivatives.

References

1.
Oxidative degradation of benzene rings
Mander L.N., Williams C.M.
Tetrahedron, 2003
2.
Supramolecular Metal−Organometallic Coordination Networks Based on Quinonoid π-Complexes
Oh M., Carpenter G.B., Sweigart D.A.
Accounts of Chemical Research, 2003
5.
Masked o-benzoquinones in organic synthesis.
Liao C., Peddinti R.K.
Accounts of Chemical Research, 2002
8.
Structures of some condensation products of .alpha.-dicarbonyl compounds and tris(amino)phosphines in solution
Denney D.B., Denney D.Z., Hammond P.J., Tseng K.
Journal of the American Chemical Society, 1981
9.
Some caged oxaazaphosphoranes
Denney D.B., Denney D.Z., Gavrilovic D.M., Hammond P.J., Huang C., Tseng K.
Journal of the American Chemical Society, 1980
13.
Organophosphorus Compounds in Reactions with Quinones
Kutyrev A.A., Moskva V.V.
Russian Chemical Reviews, 1987
14.
Reactions of α-Diketones and o-Quinones with Phosphorus Compounds
Osman F.H., El-Samahy F.A.
Chemical Reviews, 2002
15.
Antiprotozoal quinones. II. Synthesis of 4-amino-1,2-naphthoquinones and related compounds as potential antimalarials
Bullock F.J., Tweedie J.F., McRitchie D.D., Tucker M.A.
Journal of Medicinal Chemistry, 1970
18.
Synthesis and PTP1B inhibition of 1,2-naphthoquinone derivatives as potent anti-diabetic agents
Ahn J.H., Cho S.Y., Ha J.D., Chu S.Y., Jung S.H., Jung Y.S., Baek J.Y., Choi I.K., Shin E.Y., Kang S.K., Kim S.S., Cheon H.G., Yang S., Choi J.
Bioorganic and Medicinal Chemistry Letters, 2002
19.
10.1016/j.mencom.2007.05.018_bib10
Bogdanov
Zh. Org. Khim., 2005
20.
10.1016/j.mencom.2007.05.018_bib11
Pudovik
Zh. Obshch. Khim., 1976
21.
10.1016/j.mencom.2007.05.018_bib12
Pudovik
Zh. Obshch. Khim., 1973
22.
E-map improvement in direct procedures
Altomare A., Cascarano G., Giacovazzo C., Viterbo D.
Acta Crystallographica Section A Foundations of Crystallography, 1991
23.
L. H. Straver and A. J. Schierbeek, MOLEN. Structure Determination System. Nonius B.V., Delft, The Netherlands, 1994, vols. 1, 2.
24.
WinGXsuite for small-molecule single-crystal crystallography
Farrugia L.J.
Journal of Applied Crystallography, 1999
25.
10.1016/j.mencom.2007.05.018_bib16
Spek
Acta Crystallogr., Sect. A, 1990