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Chapter 15-2 - CHEM 262 Wei You Chapter 15 Organometallic...

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Chapter 15. Organometallic Compounds (2) CHEM 262 Wei You
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2 Gilman Reagents Lithium diorganocopper reagents, known more commonly as Gilman reagents prepared by treating an alkyl, aryl, or alkenyl lithium compound with Cu(I) iodide 2 CH 3 CH 2 CH 2 CH 2 Li + CuI or THF diethyl ether ( CH 3 CH 2 CH 2 CH 2 ) 2 Cu -  Li  + + LiI Butyllithium Copper(I)   iodide Lithium dibutylcopper      (a Gilman reagent)
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3 Rxns of Gilman Reagents Can form new carbon-carbon bonds by coupling Gilman Reagents with alkyl and alkenyl chlorides, bromides, and iodides I 1. Li, pent ane 2. CuI CuLi Br 2-Methyl-1-dodecene 1-Iododecane or THF diethyl ether 2 R'Br R 2 CuLiBr R'-R RCu LiBr or THF diethyl ether + + + Example
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4 Gilman Reagents coupling with a vinylic halide is stereospecific ; the configuration of the carbon-carbon double bond is retained I CuLi 2 diethyl ether + or THF Lithium dibutylcopper trans- 1-Iodo-1-nonene trans- 5-Tridecene
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5 Rxns with Gilman Reagents Reaction with epoxides involves
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