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- Title
Synthesis of Phosphorus-Containing Podands―Analogs of Diglycolamide Based on Diphenyl- and Dibutylphosphorylmethanol under Phase Transfer Catalysis Conditions.
- Authors
Kharlamov, A. V.; Belus, S. K.; Artyushin, O. I.; Bondarenko, N. A.
- 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.
- Subjects
PHOSPHORUS compound synthesis; METHANOL; PHASE-transfer catalysis; ALKYLATION; METHYL ether synthesis; CARBAMOYL compounds; PHOSPHORYL group; TRANSESTERIFICATION
- Publication
Russian Journal of General Chemistry, 2018, Vol 88, Issue 9, p1842
- ISSN
1070-3632
- Publication type
Article
- DOI
10.1134/S107036321809013X