Application of Active Phosphorus Species, Electrochemically Generated from Trivalent Phosphorus Compounds, to Organic Synthesis
| Project/Area Number |
60570987
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Osaka University |
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Principal Investigator |
OHMORI Hidenobu Faculty of PHarmaceutical Sciences, Osaka University, 薬学部, 助教授 (90028845)
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| Project Period (FY) |
1985 – 1986
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| Project Status |
Completed (Fiscal Year 1986)
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| Budget Amount *help |
¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1986: ¥400,000 (Direct Cost: ¥400,000)
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| Keywords | phosphine / phosphite / electrochemical oxidation / quatenary phosphonium salts / 電解合成 |
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| Research Abstract |
On electrochemical oxidation of phosphines or phosphites in the presence of various nucleophiles, were obtained the results, some of which are expected to be synthetically useful.
1. Reactions of triphenylphosphine radical cation with olefins gave the following phosphonium salts: 1-alkenyltriphenyl-, allyltriphenyl-, 3-oxoalkyltriphenyl-, and <beta> -ketotriphenylphosphonium salts. Reaction of the radical cation with 1,3-dicarbonyl compounds afforded the corresponding phosphoranes. These reactions were all performed in one-step procedures.
2. Simple, one-step preparation of thioalkoxytributylphosphonium salts was effected. The phosphonium salts are potential agents for the synthesis of thiol esters and unsymmetrical sulfides.
3. Indirect electrochemical oxidation of trialkylphosphites was examined. However, no mediator really effective for the reaction could be found yet, except for the observation that dialkyldisulfides may assist the oxidation to result in the anodic substitution of trialkylphosphites. Further study on the point is required.
4. Electrochemical oxidation of phosphine - <SCN^-> system has been found to be applicable for some synthetic reactions such as alkylthiocyanate formation and electrochemical cyanation of carbon nucleophiles. Detailed studies on the subject are in progress.
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Report
(1 results)
Research Products
(4 results)
