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Cu_Zn_Organometallics

its all about organometallic chemistry of zinc and copper metal

Gilman Limitations •

Gilman Limitations • Methyl and 1° R-X iodides work well – elimination occurs with 2° and 3 ° R-X – seems to follow S N 2 conditions • also works for vinyl and aryl halides

Organocopper compounds • Use of organocopper reagents offers a very efficient method for coupling of two different carbon moieties. • Cu is less electropositive than Li and Mg, the C–Cu bond is less polarized than the C–Li and C–Mg bonds. This difference produces three useful changes in reactivity: – organocopper reagents react with alkyl-, alkenyl-, and aryl halides to give alkylated products. – organocopper reagents: more selective and can be acylated with acid chlorides without concomitant attack on ketones, alkyl halides, and esters. – Relative reactivity: RCOCl > RCHO > tosylates, iodides > epoxides > bromides >> ketones > esters > nitriles. • In reactions with α,β-unsaturated carbonyl compounds, the organocopper reagents prefer 1,4-addition over 1,2-addition.

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