145385-15-5Relevant articles and documents
Studies on the Occurence of Hydrogen Transfer. 65. The Significance of Solvents and Solvent Mixtures in the Reductive Cleavage of Compounds of the Type ArSO2Y (Y= OR, Ar', Cl) with Alkali Amalgams
Horner, Leopold,Schmitt, Rolf-Erhard
, p. 469 - 474 (2007/10/02)
The dependence of the yields of the reductive fission of hexyl benzenesulfonate and mesitylphenyl sulfone with alkali-metal amalgams (primarily lithium amalgam) was studied under standard conditions in toluene using a series of eight aprotic and six protic solvents as cosolvents.Yields about 5percent were measured in toluene, but addition of equimolar amounts (w.r.t. ester or sulfone) of the alcohols methanol, ethanol, isopropyl alcohol or tert-butyl alcohol as co-solvent raised the yields to 80 - 100percent (Fig. 1).In toluene, portion-wise addition of substoichiometric amounts (w.r.t ester) of the cosolvent DMF, THF, dioxane and isopropyl alcohol resulted in the values recorded in Fig. 2.The observed effects are attributed to the different solubilities of Li+-solutions (of unknown composition) in toluene.A reaction mechanism for the reductive fission of ArSO2Y (Y = OR, Ar', Cl) with alkali-metal amalgams is proposed.