Add time:07/24/2019         Source:sciencedirect.com

The reaction of Me3GeC6H5 and Me3GeC6H4Me with Me2CH+, Me3C+, and Me2Cl+ has been studied in the gas phase at pressures spanning from 1 Torr (chemical ionization mass spectrometry) to 1 atm (radiolytic technique). The reactions conform to the general model of electrophilic aromatic substitution reactions, proceeding via σ-complex intermediates, which show a tendency to isomerize to arenium ions bearing a proton on the germylated carbon. Such 1,2-H shift processes occur in the time scale of 10−8 s. The fate of the germylated arenium ions is controlled by competing deprotonation and degermylation reactions showing a behavior similar to their silicon analogues. The Me3X (X = Si, Ge) groups are seen to show a comparable electronic effect with regard to electrophilic attack at the unsubstituted ring positions of an attached phenyl group.

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