Abstract
Oxidation of 10-hydroxy-2,8-dimethyl-10H-10λ5-phenoxaphosphine 10-oxide (1) with potassium permanganate in an alkaline medium afforded 10-hydroxy-10-oxo-10H-10λ5-phenoxaphosphine-2,8-dicarboxylic acid (2). The latter exists as a stable crystal hydrate containing two water molecules. With the aim of examining the possibility of performing the synthesis of polybenzoazoles based on acid 2, the model reaction of the latter with o-phenylenediamine in polyphosphoric acid (PPA) was studied. New high-molecular-weight phosphorus-containing polybenzoimidazoles were prepared by the reaction of 2 with various aromatic tetraamines in PPA and Eaton’s reagent.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
A. L. Rusanov, D. Yu. Likhachev, and K. Mullen, Usp. Khim., 2002, 71, 862 [Russ. Chem. Rev., 2002, 71 (Engl. Transl.)].
K. U. Buhler, Spezialplaste, Akademie Verlag, Berlin, 1978, 1015 pp.
V. V. Korshak, N. M. Kozyreva, and A. I. Kirilin, Uspekhi khimii v oblasti elementoorganicheskikh polimerov [Advances in Chemistry of Organometallic Polymers], Nauka, Moscow, 1988, 320 pp. (in Russian).
US Pat. 4634530; Chem. Abstr., 1987, 106, 15770lj.
J.-T. Wang, S. Wasmus, and R. F. Savinell, J. Electrochem. Soc., 1996, 143, 1233.
S. R. Samms, S. Wasmus, and R. F. Savinell, J. Electrochem. Soc., 1996, 143, 1225.
R. F. Savinell, E. Yeager, D. Tryk, U. Landau, J. S. Wainright, D. Weng, K. Lux, M. Litt, and C. Rogers, J. Electrochem. Soc., 1994, 141, L46.
G. M. Kosolapoff, Organic Phosphorus Compounds, John Wiley and Sons, Inc., New York, 1976, 7, 16.
L. D. Freedman, G. O. Doak, and J. E. Edmisten, J. Org. Chem., 1961, 26, 284.
I. I. Ponomarev, Yu. Yu. Rybkin, and E. I. Goryunov, Tez. dokl. X Vseross. konf. “Struktura i dinamika molekulyarnykh sistem” [Abstrs. of Papers, X All-Russian Conf. “Structure and Dynamics of Molecular Systems”] (Yalchik lake, June 30–July 4, 2003), Marii-El Republic, 2003, 254 (in Russian).
P. E. Eaton, G. R. Carlson, and J. T. Lee, J. Org. Chem., 1973, 38, 4071.
J. K. Still and T. W. Campbell, Condensation Monomers, John Wiley and Sons, Inc., New York, 1972, 632 pp.
Author information
Authors and Affiliations
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1937–1941, September, 2004.
Rights and permissions
About this article
Cite this article
Ponomarev, I.I., Rybkin, Y.Y., Goryunov, E.I. et al. Synthesis and properties of 10-hydroxy-10-oxo-10H-10λ5-phenoxaphosphine-2,8-dicarboxylic acid and related polybenzoimidazoles. Russ Chem Bull 53, 2020–2024 (2004). https://doi.org/10.1007/s11172-005-0065-2
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-005-0065-2
Key words
- 10-hydroxy-2,8-dimethyl-10H-10λ5-phenoxaphosphine 10-oxide
- oxidation with potassium permanganate
- 10-hydroxy-10-oxo-10H-10λ5-phenoxaphosphine-2,8-dicarboxylic acid
- polycondensation
- o-phenylenediamine
- polyphosphoric acid
- Eaton’s reagent
- aromatic tetraamines
- 1,2-diamino-4-(3,4-diaminophenoxy)-benzene
- 1,2-diamino-(3,4-diaminophenylsulfonyl)benzene
- phosphorus-containing polybenzoimidazoles