Anionic rearrangement of the germyl and silyl groups in dimethylammonium N-methylide and related compounds

Article abstract of DOI:10.1016/0022-328X(89)88037-4

The reaction of <2,2-bis(trimethylsilyl)ethyl>- and <2,2-bis(trimethylgermyl)ethyl>trimethylammonium iodides (3a and 3c) with n-butyllithium gives N-<(trimethylsilyl)methyl>- and N-<(trimethylgermyl)methyl>dimethylamines (5a and 5b), respectively.A mixture of 5a and 5b is obtained from the reaction of <2-(trimethylgermyl)-2-(trimethylsilyl)ethyl>trimethylammonium iodide (3b).Use of lithium diisopropylamide in place of n-butyllithium gives the corresponding 1,1-bis(trimethylelemento)ethylenes (8a, 8b, and 8c) as the main products.