|
Main Index Search Register Login Who's Online FAQ Links | |
||
|
|
|||
|
||||
| 1 Online, 0 Active | You are not logged in | |||
|
|
Methods Discourse | |
|
|
|
|
All 6 posts | Subject: Oxidation of terminal olefins with Tetrakis(Triphenylphosphine)Palladium(0) | Please login to post | Down | |
|||
|
|
|
|
|
|||||||
|
Slappy (Moderator) 08-31-99 11:37 No 103613 |
|
Oxidation of terminal olefins with Tetrakis(Triphenylphosphine)Palladium(0) (Rated as: good read) |
||||||
|
Oxidation of terminal olefins with Tetrakis(Triphenylphosphine)Palladium(0) Gazz Chim Ital 122, 531-532 (1992) (English) Solvent: 3.2M aqueous H2O2 solution. Reaction conditions: 72h stirring at ~50°C. Catalysis statistics: 2000:1 molar ratio alkene:catalyst Conversion & Selectivity: 99%+ Summary- Terminal Olefins can be oxidised under mild conditions in exellent yields and selectivities to methyl ketones by employing an auqeous medium containing hydrogen peroxide as the oxidant and tetrakis(triphenylphosphine)palladium(0) as the catalyst. Palladium(0)-catalysed oxidation of terminal alkenes with Hydrogen Peroxide in a heterogeneous aqueous medium. Olefin / Product / Conversion / Selectivity / Reaction Temp. - 1-hexene / 2-hexanone / >99% / >99% / 40°C 1-heptene / 2-heptanone / >99% / >99% / 50°C 1-octene / 2-octanone / 98% / >99% / 50°C 1-decene / 2-decanone / 98% / >99% / 80°C 1-octadecene / 2-octadecanone / 10% >99% / 80°C --- Rhodium posted this in the Serious Chemistry Forum a while back. Has anyone else taken a look at this? If this will work with Safrole, and I see no reason why it wouldn't, we would have the perfect method. Minimal equipment, easy procedure, no isomerized alkene, it seems perfect to me. In case you were wondering, Tetrakis(Triphenylphosphine)Palladium(0) is used in industry, and is available from all the major chem companies (Alfa, TCI, Etc.) for a fair price, about the same or cheaper than PdCl2. Plus, you are using only a fraction of the amount (5g for 100g olefin as opossed to 500mg for 100g olefin). And it is totally unwatched. Any thoughts/comments? I am going to try and give it a runs as soon as I can get my hands on the catalyst. |
||||||||
|
|
|||||||
|
|
|
|||||||
|
Rhodium (Administrator) 08-31-99 22:39 No 103614 |
|
Re: Oxidation of terminal olefins with Pd(PPh3)4 | ||||||
|
I spoke with someone who tried the method, but didn't give much details. His only tip was to run the reaction at 25-30°C until TLC (hexane/ethyl acetate 4:1) showed that the starting material was consumed, then do the workup. Too high rxn temps apparently messed things up. |
||||||||
|
|
|||||||
|
|
|
|||||||
|
r2d3 (Member) 09-01-99 00:46 No 103615 |
|
Re: Oxidation of terminal olefins with Tetrakis(Triphenylphosphine)Palladium(0) | ||||||
|
Rho: Did he mention the size of the reaction. With 72+ hours reaction time, the small volume seems to be the only drawback. |
||||||||
|
|
|||||||
|
|
|
|||||||
|
Rhodium (Administrator) 09-01-99 12:54 No 103616 |
|
Re: Oxidation of terminal olefins with Tetrakis(Triphenylphosphine)Palladium(0) | ||||||
|
Nope, the only additional info he gave was that he used hexane/ethyl acetate 4:1 for the TLC 
|
||||||||
|
|
|||||||
|
|
|
|||||||
|
Rhodium (Chief Bee) 03-19-04 16:28 No 496153 
|
|
Super clean wacker variation | ||||||
|
This reaction deserves a *bump* to the forum top. Anyone have the full article in PDF? The Hive - Clandestine Chemists Without Borders |
||||||||
|
|
|||||||
|
|
|
|||||||
|
lugh (Moderator) 03-24-04 01:56 No 496943 |
|
Ioele's paper (Rated as: good read) |
||||||
|
Ioele et al's paper in Deja Vu format: Gazz Chim Ital 122, 531-532 (1992)
Chemistry is our Covalent Bond |
||||||||
|
|
|||||||