ArticleMolecules (Basel, Switzerland)2021
Tetraalkyl Hydroxymethylene-bisphosphonate and Dialkyl 1-Diphenylphosphinoyl-1-hydroxy-ethylphosphonate Derivatives by the Pudovik Reaction and Their Rearranged Products.
Article in Molecules (Basel, Switzerland), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- The Synthesis of α-Hydroxy-Alkylphosphonate Derivatives and Evaluation of Their Cytotoxic Activity.Pharmaceuticals (Basel, Switzerland) · 2026Article
- The surprising reaction of (chloro- and methanesulfonyloxy)(phenyl)methylphosphonates and -(phenyl)methylphosphine oxides with potassium diphenylphosphide followed by oxidation.Beilstein journal of organic chemistry · 2026Article
- Conformational Analysis of 1,5-Diaryl-3-Oxo-1,4-Pentadiene Derivatives: A Nuclear Overhauser Effect Spectroscopy Investigation.International journal of molecular sciences · 2023Article
- A Study of the Bisphosphonic Derivatives from the Pudovik Reaction of Dialkyl α-Oxophosphonates and >P(O)H Reagents: X-ray Structure and Bioactivity.Molecules (Basel, Switzerland) · 2023Article
- Organophosphorus Chemistry 2021.Molecules (Basel, Switzerland) · 2023Article
- Design and Synthesis of New α-hydroxy β-fluoro/β-trifluoromethyl and Unsaturated Phosphonates from Carbohydrate-Derived Building Blocks via Pudovik and Horner-Wadsworth-Emmons Reactions.Molecules (Basel, Switzerland) · 2022Article
Corrections and comments
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Authors and funding
2 authors.
Funding
Abstract
The reaction of diethyl α-oxoethylphosphonate and diethyl oxobenzylphosphonate with diethyl phosphite, dimethyl phosphite, and diphenylphosphine oxide affords, depending on the substrates and conditions (nature and quantity of the amine catalyst, temperature, and solvent), the Pudovik adduct and/or the corresponding >P(O)-CH-O-P(O)< product formed by rearrangement. The nature of the substituent on the central carbon atom (a methyl or phenyl group) influences the inclination for the rearrangement. The asymmetric products (either adducts or rearranged species) with different P(O)Y functions (Y = RO or Ph) exhibit interesting NMR features.
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Registered trials
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