THE METALATION OF N,N,N',N'-TETRAMETHYLETHYLENEDIAMINE (TMEDA) Academic Article

abstract

• The Metalation of N,N,N,N,Tetramethylethylenediamine (TMEDA) TMEDA may be metalated with good regioselectivity: tertBuLi attacks preferably a methyl group whereas a methylene group is deprotonated by nBuLi/tertBuOK. Thus, trapping with Me3SnCl and hydrolytic workup give either 53% of Me2N[CH2]2NMe(CH2SnMe3) (2) and 5% of (Me3Sn)(Me2N)CCH2 (3) or 3 alone (42%), respectively. 3 is formed from deprotonated TMEDA by elimination of amide which can be trapped as Me2N(SnMe3) (5); some trans(Me3Sn)CHCH(NMe2) (4) is also obtained. The structures of the compounds follow mainly from 1H, 13C, 15N, and 119SnNMR data. Copyright 1987 WILEYVCH Verlag GmbH & Co. KGaA, Weinheim

authors

• Bluemel, Janet

published proceedings

• CHEMISCHE BERICHTE-RECUEIL

author list (cited authors)

• KOHLER, F. H., HERTKORN, N., & BLUMEL, J.

citation count

• 64

complete list of authors

• KOHLER, FH||HERTKORN, N||BLUMEL, J

publication date

• January 1987

publisher

• Wiley  Publisher

published in

• Chemische Berichte  Journal

Digital Object Identifier (DOI)

• 10.1002/cber.19871201220

start page

• 2081

end page

• 2082

volume

• 120

issue

• 12

URL

• http%3A%2F%2Fdx.doi.org%2F10.1002%2Fcber.19871201220