Synthesis of Phosphorus-Containing Podands―Analogs of Diglycolamide Based on Diphenyl- and Dibutylphosphorylmethanol under Phase Transfer Catalysis Conditions
- Authors: Kharlamov A.V.1, Belus S.K.1, Artyushin O.I.2, Bondarenko N.A.1
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Affiliations:
- Institute of Chemicals and High Purity Compounds
- Nesmeyanov Institute of Organolement Compounds
- Issue: Vol 88, No 9 (2018)
- Pages: 1842-1849
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/222411
- DOI: https://doi.org/10.1134/S107036321809013X
- ID: 222411
Cite item
Abstract
A convenient method for preparation of phosphorus-containing podands R2P(O)CH2OCH2X, where X = C(O)NBu2; P(O)R′2, R = R′ = Ph, Bu, R = Ph, R′ = Bu via OH-alkylation of phosphorylmethanols under the phase transfer conditions in the presence of Cs2CO3 was developed. Carbamoyl-substituted dimethyl ethers were synthesized via transformation of phosphorylmethanols to phosphorylmethoxyacetic acids, followed by amidation. Symmetrical bisphosphoryl substituted dimethyl ethers were obtained by reaction of phosphorylmethanols with tosyl chloride in the presence of Cs2CO3. The synthesis of unsymmetrical substituted ether in the presence of Cs2CO3 was complicated by transesterification of phosphorylmethyl tosylate resulting in the formation of symmetrical dimethyl ethers as byproducts.
About the authors
A. V. Kharlamov
Institute of Chemicals and High Purity Compounds
Email: bond039@mail.ru
Russian Federation, Bogorodskii val 3, Moscow, 107076
S. K. Belus
Institute of Chemicals and High Purity Compounds
Email: bond039@mail.ru
Russian Federation, Bogorodskii val 3, Moscow, 107076
O. I. Artyushin
Nesmeyanov Institute of Organolement Compounds
Email: bond039@mail.ru
Russian Federation, Moscow
N. A. Bondarenko
Institute of Chemicals and High Purity Compounds
Author for correspondence.
Email: bond039@mail.ru
Russian Federation, Bogorodskii val 3, Moscow, 107076