Gilman Reagent

Gilman Reagent Reaction

Definition: What is Gilman Reagent?

Gilman reagent is an organocuprate reagent consisting of lithium, copper, and alkyl group with the molecular formula [R-Cu-R]+Li (lithium dialkylcuprate). It is used to synthesize new compounds consisting of carbon-carbon bonds from alkyl, aryl, and vinyl halides. Typically, the SN2 reaction method is employed to obtain the final product. The SN2 reaction mechanism is discussed in another article [1-7].

Gilman Reagent Reaction

The history of Gilman reagent goes back to the 1930s when American chemist Henry Gilman discovered it and reported it in a 1952 paper.

Preparation of Gilman Reagent

Gilman reagent can be prepared in two steps: First, by adding powdered lithium metal to alkyl halide in pentane solvent. Second, by adding copper(I) bromide to alkyllithium in tetrahydrofuran at −78 °C.

Gilman Reagent Preparation

Example of Gilman Reagent Reaction

Gilman reagent is used to synthesize new compounds using SN2 reaction as well as α, β – addition [1-3].

Gilman Reagent Reaction Examples

References

  1. Definition and examples – Testbook.com
  2. Definition and examples – Chem.libretexts.org
  3. Definition and example – Nptel.ac.in
  4. Definition – Chemistry.msu.edu
  5. Definition – Chem.ucla.edu
  6. Definition – Organicreactions.org
  7. Definition – Evans.rc.fas.harvard.edu

By Satyam Bhuyan

Satyam Bhuyan works as a content developer and regularly contributes to sciencefacts.net and chemistrylearner.com. He holds a Ph.D. in Mechanical Engineering and has an in-depth passion for science, especially physics and materials science. When he is not writing, he can be seen in a movie theatre or concert hall. Aside, he is an avid traveler and has lived in six countries.

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