109862-84-2Relevant academic research and scientific papers
The Metalation of N,N,N',N'-Tetramethylethylenediamine (TMEDA)
Koehler, Frank H.,Hertkorn, Norbert,Bluemel, Janet
, p. 2081 - 2082 (2007/10/02)
TMEDA may be metalated with good regioselectivity: tert-BuLi attacks preferably a methyl group whereas a methylene group is deprotonated by n-BuLi/tert-BuOK.Thus, trapping with Me3SnCl and hydrolytic work-up give either 53percent of Me2N2NMe(CH2SnMe3) (2) and 5percent of (Me3Sn)(Me2N)C=CH2 (3) or 3 alone (42percent), respectively. 3 is formed from deprotonated TMEDA by elimination of amide which can be trapped as Me2N(SnMe3) (5); some trans-(Me3Sn)CH=CH(NME2) (4) is also obtained.The structures of the compounds follow mainly from 1H-, 13C-, 15N-, and 119Sn-NMR data.
