By A. Furstner
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Additional info for Active Metals [chemistry]
Entry Alkyl bromide Elcctrophilc Product Yield (%) 95 C l 8 , YPh CIP'h CIL C 87 62 I 84 CI8 , h dPh dPh 99 CIP'h 0 CIAPh 15 . 8 Formation of Tertiary and Secondary Alkylzinc Bromides Tertiary and secondary alkylzinc bromides can be formed directly from tertiary alkyl bromides at room temperature (secondary alkyl bromides at reflux) with Rieke zinc . This is a significant result, especially for the formation of tertiary alkylzinc bromide reagents, which would be difficult or impossible by other methods, which do not have the capacity to tolerate functionality.
The activation of the zinc surface could originate by the adsorption of the Lewis base cyanide ion on the metal surface. The adsorbed cyanide ion can affect the metal's reactivity in two possible ways. One possible mode of activation would be the reduction of the metal's work function in the vicinity of the adsorbed cyanide ion, and the second could be that the cyanide ion is acting as a conduction path for the transfer of the metal's electrons to the alkyl chloride. One or both processes could account for the observed enhanced chemical reactivity.
The generation of a quaternary carbon center is not a trivial undertaking in organic synthesis, and multiple synthetic steps are often required. In work related to our studies of the synthesis of spiro-d-lactones , the preparation of alcohols and vic-diols has also been realized utilizing thls one-pot methodology . In the process the formation of a quaternary carbon center is achieved. Scheme 1-10 shows that the initial adduct 3, when treated with dilute acid at low temperature, affords the alcohol 4 containing a quaternary carbon center.
Active Metals [chemistry] by A. Furstner