By Alois Fürstner

Reactions with metals are ubiquitous in natural synthesis and, really within the previous couple of years, a wide repertoire of equipment for the activation of metals and for his or her use in natural synthesis has been constructed. In energetic Metals, issues starting from morphology of steel clusters and nanometallurgy to organometallic chemistry, catalysis and using activated metals in average product synthesis are authoritatively mentioned through prime specialists within the field.

lively Metals will let you absolutely enjoy the contemporary advances within the box by way of giving:

* special experimental procedures
* information on manipulation of lively metals less than inert atmosphere
* worthy details for making plans syntheses
* vast tables of average conversions with yields
* seriously chosen, up to date references

This guide is a special resource of 'hands-on' details with a view to let you extend the scope of your study.

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Extra info for Active Metals: Preparation*Characterization*Applications

Example text

The process presented here is a facile means for the preparation of alcohols and vicdiols in one pot in high yields. Table 1-9. Reactions of conjugated diene-magnesium reagents with epoxides followed by acidic hydrolysis. Entry Diene Epoxide F'roducta) Yieldh' (70) 86 60" 64 90 5 H 47 a) Elemental analysis, mass spectra, 'H NMR, I3C NMR, and FTIR were all consistent with the indicated formulation. b) Isolated yields. c) Yield was based on amount of active magnesium. d) A 1 : 1 mixture of diastereomers as determined by 'H NMR.

Formation of cyclopentenols. ~~ Entry l 3 o Diene = Ester Product Yielda) CH3COOEt 91 CH3(CH2)2COOEt 96 PhCOOEt 55 = a< CH3(CH2)2COOEt a) Fused bicyclic product was obtained under reflux. 59 74 16 I Rieke Metals: Highly Reactive Metal Powders Table 1-6. Reactions of diene-magnesium reagents with carboxylic esters. Formation of ketones. Entry Diene Ester Product /3. y-unsaturated Yielda' (YO) CH&X)OEt 72 CH3(CH&COOEt ni PhCOOEt 62 CH3(CH2)2COOEt 76 84 a) Quenching the reaction at - 10 "C gave the /3.

However, the resulting organocopper reagent was less nucleophilic and not efficient in reactions that require a higher degree of nucleophilicity such as intermolecular epoxide ring opening reactions. Although the choice of phosphine ligand was found to be crucial for thc formation and subsequent reactivity of the organocopper species, the presence of malodorous phosphine ligands was often found to interfere with product isolation. In our search for a more reactive copper that did not require the use of phosphorus ligands, we discovered that the 36 I Rieke Metals: Highly Reactive Metal Powders lithium napthalenide reduction of a solution of a commercially available lithium 2-thienylcyanocuprate or CuCN .

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