Gas-Phase Synthesis of Organoargenate Anions and Comparisons with Their Organocuprate Analogues

Abstract

The gas-phase double decarboxylation of the silver carboxylate centers [RCO 2AgO 2CR]- and [MeCO 2AgO 2CR]- was investigated as a means of synthesizing homo- [RAgR]- (R = Me and Et) and heteroargenates [MeAgR]- (R = Et, Pr, iPr, tBu, Allyl, PhCH 2, Ph). The formation of these organoargenates was examined by multistage mass spectrometry experiments employing collision-induced dissociation (CID) and by density functional theory. A key side reaction in competition with the second stage of decarboxylation involves the loss of the anionic carboxylate ligand. Interpretation of the decarboxylation pathway of the heterocarboxylates [MeCO 2AgO 2CR]- was more complex due to the possibility of decarbox..