Editing Gilman reagent (section)

== History ==
These reagents were discovered by [[Henry Gilman]] and coworkers.<ref>{{cite journal | title = The Preparation of Methylcopper and some Observations on the Decomposition of Organocopper Compounds| author = [[Henry Gilman]], Reuben G. Jones, and L. A. Woods| pages = 1630–1634| journal = [[Journal of Organic Chemistry]]| doi = 10.1021/jo50012a009| volume = 17| issue = 12| year = 1952}}</ref> '''Lithium dimethylcopper''' (CH<sub>3</sub>)<sub>2</sub>CuLi can be prepared by adding [[copper(I) iodide]] to [[methyllithium]] in [[tetrahydrofuran]] at −78&nbsp;°C. In the reaction depicted below,<ref>''Modern Organocopper Chemistry, '' N. Krause Ed. Wiley-VCH, 2002.</ref> the Gilman reagent is a methylating reagent reacting with an [[alkyne]] in a [[conjugate addition]], and the [[ester]] group forms a cyclic [[Alpha-beta Unsaturated carbonyl compounds|enone]].

[[Image:Gilman reaction example.png|center|400px|Scheme 1. Example Gilman reagent reaction]]

:[[File:Gilman vs Grignard.jpg|frameless|310x310px]]