Journal article

Dimethylcuprate-Mediated Transformation of Acetate to Dithioacetate

Jiawei Li, George N Khairallah, Richard AJ O'Hair

ORGANOMETALLICS | AMER CHEMICAL SOC | Published : 2015

Abstract

Dithiocarboxylic acids, RCS2H, and their esters, RCS2R′, are useful reagents that can be synthesized by the reaction of carbon disulfide with organometallic reagents. Here the coinage-metal-mediated transformation of acetate to dithioacetate is explored in the gas phase using multistage mass spectrometry experiments in a linear ion trap mass spectrometer in conjunction with density functional theory (DFT) calculations. The ion-molecule reactions between coinage-metal dimethylmetalate anions [CH3MCH3]- (M = Au, Ag, Cu), formed via double decarboxylation of the metal acetate anions, [CH3CO2MO2CCH3]-, and carbon disulfide, were examined. Only [CH3CuCH3]- reacts with CS2 with a reaction efficien..

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