|

Features of Dismutation of Aryldichlorphosphites

Authors: Slitikov P.V. Published: 28.04.2022
Published in issue: #2(101)/2022  
DOI: 10.18698/1812-3368-2022-2-102-111

 
Category: Chemistry | Chapter: Physical Chemistry  
Keywords: dismutation, phosphorous acid chlorides, thermodynamic state functions, computer simulation

Abstract

The paper considers the spontaneous rearrangement, i.e., dismutation, of phosphorous acid dichlorides (aryl dichlorophosphites) into acid chlorides (diaryl chlorophosphites) with separation of phosphorus trichloride. The starting materials contained phenyl, 1- and 2-naphthols as aromatic radicals. The main patterns of dismutation of aryldichlorophosphites were revealed and the basic factors influencing the process time were determined. The dismutation parameters of aryldichlorophosphites were compared with the regularities revealed earlier for a similar process with the participation of diamidoesters of phosphorous acid containing phenyl and naphthyl substituents as an ether component. Calculations of thermodynamic functions of state, i.e., standard enthalpies of ΔfH0298 formation and S0298 entropies, for the dismutation participants, standard values of the Gibbs energy of ΔrG0298 reactions, were calculated. Calculations were carried out without taking into account the influence of the solvent and for the case of standard conditions, as well as for similar systems --- diamidoesters of phosphorous acid. The calculations allowed us to show the thermodynamic possibility of implementing dismutation of aryl dichlorophosphites at relatively low temperatures. The semi-empirical calculation method (RM1) made it possible to establish the lowest-energy conformations of diaryl chlorophosphites formed as a result of dismutation and show their fundamental difference

Please cite this article in English as:

Slitikov P.V. Features of dismutation of aryldichlorphosphites. Herald of the Bauman Moscow State Technical University, Series Natural Sciences, 2022, no. 2 (101), pp. 102--111 (in Russ.). DOI: https://doi.org/10.18698/1812-3368-2022-2-102-111

References

[1] Corbridge D.E.C. Phosphorus. Chemistry, biochemistry and technology. CRC Press, 2013.

[2] Free M.L. Hydrometallurgy. Fundamentals and applications. Wiley, 2013.

[3] Duda A., Kubisa P., Lapienis G., et al. Milestones in development of a ring-opening polymerization of the heterocyclic monomers --- view from a personal perspective. Polimery, 2014, vol. 59, no. 1, pp. 9--23.

[4] Salmeia K.A., Gaan S., Malucelli G. Recent advances for flame retardancy of textiles based on phosphorus chemistry. Polymers, Special Iss.: Recent Advances in Flame Retardancy of Textile Related Products, 2016, vol. 8, iss. 9, art. 319. DOI: https://doi.org/10.3390/polym8090319

[5] Schartel B. Phosphorus-based flame retardancy mechanisms --- old hat or a starting point for future development? Materials, Special Iss.: Flame Retardants, 2010, vol. 3, iss. 10, pp. 4710--4745. DOI: https://doi.org/10.3390/ma3104710

[6] Kamer P.C.J., Leeuwen P.W.N.M. Phosphorus(III) ligands in homogeneous catalysis. Design and synthesis. Wiley, 2012.

[7] Nifantyev E.E., Grachev M.K., Burmistrov S.Yu. Amides of trivalent phosphorus acids as phosphorylating reagents for proton-donating nucleophiles. Chem. Rev., 2000, vol. 100, iss. 10, pp. 3755--3799. DOI: https://doi.org/10.1021/cr9601371

[8] Tolkmith H. Aromatic phosphorodichloridites and phosphorodichloridothioates. I. Aryl phosphorodichloridites. J. Org. Chem., 1958, vol. 23, iss. 11, pp. 1682--1684. DOI: https://doi.org/10.1021/jo01105a025

[9] Slitikov P.V. [Particular dismutation cases of trivalent phosphor derivatives using the example of aryldichlorophosphites]. 11-ya Vseros. konf. "Neobratimye protsessy v prirode i tekhnike". Ch. 1 [11th Russ. Conf. "Irreversible Processes in Nature and Technics". P. 1]. Moscow, BMSTU Publ., 2021, pp. 79--82 (in Russ.).

[10] Fattori D., Henry S., Vogel P. The Demjanov and Tiffeneau --- Demjanov one-carbon ring enlargements of 2-aminomethyl-7-oxabicyclo[2.2.1]heptane derivatives. The stereo- and regioselective additions of 8-oxabicyclo[3.2.1]oct-6-en-2-one to soft electrophiles. Tetrahedron, 1993, vol. 49, iss. 8, pp. 1649--1664. DOI: https://doi.org/10.1016/S0040-4020(01)80352-5

[11] Sun H., Yang J., Amaral K.E., et al. Synthesis of a new transition-state analog of the sialyl donor. Inhibition of sialyltransferases. Tetrahedron Lett., 2001, vol. 42, iss. 13, pp. 2451--2453. DOI: https://doi.org/10.1016/S0040-4039(01)00204-0

[12] Hatcher M.A., Posner G.N. [3,3]-Sigmatropic rearrangements: short, stereocontrolled syntheses of functionalized vitamin D3 side-chain units. Tetrahedron Lett., 2002, vol. 43, iss. 28, pp. 5009--5012. DOI: https://doi.org/10.1016/S0040-4039(02)00904-8

[13] Russell A.E., Miller S.P., Morken J.P. Efficient Lewis acid catalyzed intramolecular Cannizzaro reaction. J. Org. Chem., 2000, vol. 65, iss. 24, pp. 8381--8383. DOI: https://doi.org/10.1021/jo0010734

[14] Fluck E., van Waser J.R., Groenweghe L.C.D. Principles of phosphorus chemistry. VIII. Reorganization of triply connected monophosphorus compounds. J. Am. Chem. Soc., 1959, vol. 81, iss. 24, pp. 6363--6366. DOI: https://doi.org/10.1021/ja01533a005

[15] Brown M.P., Silver H.B. An improved method of preparation for diphenylchlorophosphine. Chem. Ind., 1961, no. 1, pp. 24--27.

[16] Slitikov P.V. Thermodynamic evaluation of diamidophosphite dismutation capability. Herald of the Bauman Moscow State Technical University, Series Natural Sciences, 2017, no. 6 (75), pp. 96--102 (in Russ.). DOI: https://doi.org/10.18698/1812-3368-2017-6-96-102

[17] Slitikov P.V. Thermodynamic aspects of naphthyldiamidophosphite dismutation. J. Phys.: Conf. Ser., 2019, vol. 1348, art. 012074. DOI: https://doi.org/10.1088/1742-6596/1348/1/012074

[18] Nifantyev E.E., Rasadkina E.N., Slitikov P.V., et al. Dismutation of diamido-arylphosphites. Phosphorus, Sulfur, Siliсon Relat. Elem., 2003, vol. 178, iss. 11, pp. 2465--2477. DOI: https://doi.org/10.1080/714040960

[19] Rasadkina E.N., Slitikov P.V., Nifant’ev E.E. Dismutation of arylene phosphorodiamidites: specific features and aspects of preparative use. Russ. J. Gen. Chem., 2006, vol. 76, pp. 183--197. DOI: https://doi.org/10.1134/S1070363206020046

[20] Nalibaeva A.M. Sintez i svoystva novykh ftorsoderzhashchikh atsiklicheskikh i tsiklicheskikh fosfitov i fosfatov. Dis. kand. khim. nauk [Synthesis and properties of new fluorine-containing acyclic and cyclic phosphites and phosphates. Cand. Sc. Eng. Diss.]. Irkutsk, IrICh, 2021 (in Russ.).

[21] Rocha G.B., Freire R.O., Simas A.M., et al. RM1: a reparatemerization of AM1 for H, C, N, O, P, S, F, Cl, Br and I. J. Comp. Chem., 2006, vol. 27, iss. 10, pp. 1101−1111. DOI: https://doi.org/10.1002/jcc.20425