Mechanism of reduction of trityl halides by lithium dialkylamide bases

M Newcomb, TR Varick, SH Goh

Index: Newcomb, Martin; Varick, Thomas R.; Goh, Swee-Hock Journal of the American Chemical Society, 1990 , vol. 112, # 13 p. 5186 - 5193

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Citation Number: 25

Abstract

Abstract: Trityl chloride (TCI) and bromide are reduced by hindered lithium dialkylamide bases in THF to give predominantly triphenylmethane and a small amount of trityl dimer. Rate constants for the reduction of TCI by lithium diisopropylamide and lithium tert- butylethylamide in THF at-78 OC have been measured; the reactions are first order in monomeric base and in trityl chloride. Inter-and intramolecular kinetic isotope effect ...

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