Leaving group dependence of the rates of halogen-magnesium exchange reactions

Organic Letters
Lei ShiHerbert Mayr

Abstract

Relative reactivities and absolute rate constants of the reactions of haloarenes with i-PrMgCl·LiCl were investigated in THF at 0 °C. The rate of the halogen-magnesium exchange decreases in the series ArI > ArBr > ArCl (relative reactivities: 10(11):10(6):1). Preliminary experiments show that the p-tolylsulfinyl group is exchanged slightly faster than iodide, while a tosyl group is exchanged at least 10(4) times more slowly than a bromide.

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Mar 14, 2009·The Journal of Organic Chemistry·Lei ShiHerbert Mayr
Jul 16, 2009·Organic Letters·Lei ShiHerbert Mayr

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Citations

Nov 6, 2013·Chemical Reviews·David TillyPhilippe C Gros
Feb 26, 2015·Chemical Communications : Chem Comm·Robert Li-Yuan BaoLei Shi
Sep 20, 2018·Chemistry : a European Journal·Dorothée S ZieglerPaul Knochel
Jan 3, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Se Ryeon LeeAnne J McNeil
Oct 21, 2017·Angewandte Chemie·Kilian ColasAbraham Mendoza
Feb 5, 2014·The Journal of Organic Chemistry·S Kyle SontagJason Locklin

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