Perfluoroalkyl iodides such as C8F17I are one of the cheapest fluorous starting materials, and it is always interesting to see papers describing synthesis of perfluoroalkyl substituted molecules from those iodides. A recent communication (Synlett 2010, 281-285, doi:10.1055/s-0029-1219169) by Prof. Ma and coworkers reports synthesis of various allenyl perfluoroalkyl ketone from allenyl esters and perfluoroalkyl Grignard reagents.
The Grignard reagents were prepared in situ by Rf-I and PhMgBr, and it was reacted with various allenyl esters. Quite interestingly, they obtained the corresponding ketones (mono-addition product), but no tertiary alcohol (the double addition product) was detected. They indeed treated one of the ketones with C4F9-MgX, and found no reaction.
One of the allenyl ketone was also derived to various molecules including C4F9 substitutes furan as shown below. Please take a look at the communication for further details, and experimental procedures.
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