Organometallic compounds, also reagents

Most other organometallic compounds also react with oxygen. Aryllithium reagents have been converted to phenols by treatment with oxygen. Trialkylboranes and alkyldichloroboranes (RBCI2) can be conveniently converted to hydroperoxides by... 

Two other acid derivatives may also be converted to ketones by reaction with organometallic compounds. Grignard reagents add to nitriles to give imine salts (Section 14.4.3), which are hydrolyzed to ketones in the reaction work-up. In Figure 19.27, again the disconnected bond is highlighted in red. Remember than many aliphatic nitriles are readily prepared by displacement... 

Organolithium reagents are also valuable in the synthesis of other organometallic compounds via... 

Bromo compounds are useful intermediates for the synthesis of a range of more complicated organic compounds via direct substitution or by prior conversion into organometallic reagents. They therefore hold a key position in the synthesis of fine chemicals. This position demands that more selective methods for the synthesis of bromo compounds also be developed. In this report we have illustrated the development of selected syntheses of bromoaromatic compounds and demonstrated new ways in which they can be applied in synthetic procedures. 

It might be mentioned that matters are much simpler for organometallic compounds with less-polar bonds. Thus Et2Hg and EtHgCl are both definite compounds, the former is a liquid and the latter is a solid. Organocalcium reagents are also known, and they are formed from alkyl halides via a single electron transfer (SET) mechanism with free-radical intermediates. "... 

Ge, P, As, Sb, and Bi, can also be prepared in this manner." Except for alkali metal alkyls and Grignard reagents, the reaction between RM and M X is the most conunon method for the preparation of organometallic compounds." ... 

Anodic processes can also be used for tetraethyllead electrosynthesis. Here solutions of organometallic compounds are used the overall reaction is replacement of the metal in these compounds by another metal, lead. One such process uses a melt of the compound NaAl(C2H5)4, from which radicals QHj are produced anodically. The process is highly efficient, but it is not easy to isolate the TEL produced from the melt. More convenient is a commercial process involving the anodic oxidation of the Grignard reagent C2H5MgCl ... 

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