Tetraalkyl Hydroxymethylene-bisphosphonate and Dialkyl 1-Diphenylphosphinoyl-1-hydroxy-ethylphosphonate Derivatives by the Pudovik Reaction and Their Rearranged Products
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.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2021 |
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| Erschienen: |
2021 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:26 |
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| Enthalten in: |
Molecules (Basel, Switzerland) - 26(2021), 24 vom: 14. Dez. |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Szalai, Zsuzsanna [VerfasserIn] |
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| Links: |
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| Themen: |
α-oxophosphonate |
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| Anmerkungen: |
Date Completed 27.12.2021 Date Revised 28.12.2021 published: Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.3390/molecules26247575 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM33482561X |
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| 245 | 1 | 0 | |a Tetraalkyl Hydroxymethylene-bisphosphonate and Dialkyl 1-Diphenylphosphinoyl-1-hydroxy-ethylphosphonate Derivatives by the Pudovik Reaction and Their Rearranged Products |
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| 500 | |a Date Completed 27.12.2021 | ||
| 500 | |a Date Revised 28.12.2021 | ||
| 500 | |a published: Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a 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 | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a 1-phosphinoyl-1-hydroxy-ethylphosphonate | |
| 650 | 4 | |a Pudovik reaction | |
| 650 | 4 | |a dialkyl phosphite | |
| 650 | 4 | |a diphenylphosphine oxide | |
| 650 | 4 | |a hydroxymethylene-bisphosphonate | |
| 650 | 4 | |a rearrangement | |
| 650 | 4 | |a α-oxophosphonate | |
| 700 | 1 | |a Keglevich, György |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Molecules (Basel, Switzerland) |d 2004 |g 26(2021), 24 vom: 14. Dez. |w (DE-627)NLM172073448 |x 1420-3049 |7 nnns |
| 773 | 1 | 8 | |g volume:26 |g year:2021 |g number:24 |g day:14 |g month:12 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.3390/molecules26247575 |3 Volltext |
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