Dimethylcuprate-Mediated Transformation of Acetate to Dithioacetate
Jiawei Li, George N Khairallah, Richard AJ O'Hair
ORGANOMETALLICS | AMER CHEMICAL SOC | Published : 2015
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..View full abstract
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Awarded by ARC
We thank the ARC for financial support via grant DP110103844 (to R.AJ.O. and G.N.K.) and DP1096134 (to G.N.K.) and through the ARC CoE program. The authors gratefully acknowledge the generous allocation of computing time from the Melbourne University high performance computing Facility (Edward).