Synthesis of Phosphorus-Containing Podands―Analogs of Diglycolamide Based on Diphenyl- and Dibutylphosphorylmethanol under Phase Transfer Catalysis Conditions

A convenient method for preparation of phosphorus-containing podands R 2 P(O)CH 2 OCH 2 X, where X = C(O)NBu 2 ; 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 Cs 2 CO 3 was developed. Carbamoyl-substituted...

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Bibliographic Details
Published in:Russian journal of general chemistry 2018-09, Vol.88 (9), p.1842-1849
Main Authors: Kharlamov, A. V., Belus, S. K., Artyushin, O. I., Bondarenko, N. A.
Format: Article
Language:English
Subjects:
Alkylation
Catalysis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Dimethyl ether
Ethers
Phosphorus
Substitutes
Synthesis
Transesterification
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Summary:A convenient method for preparation of phosphorus-containing podands R 2 P(O)CH 2 OCH 2 X, where X = C(O)NBu 2 ; 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 Cs 2 CO 3 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 Cs 2 CO 3 . The synthesis of unsymmetrical substituted ether in the presence of Cs 2 CO 3 was complicated by transesterification of phosphorylmethyl tosylate resulting in the formation of symmetrical dimethyl ethers as byproducts.
ISSN:1070-3632
1608-3350
DOI:10.1134/S107036321809013X