Tetrakis(dimethylamino)ethylene

Tetrakis(dimethylamino)ethylene (TDAE) is an organic compound with the formula [C(NMe2)2]2 (where Me = CH3), classified as an enamine. It is a colorless liquid. Primary and secondary enamines tend to isomerize, but tertiary enamines are kinetically stable. The unusual feature of TDAE is that it is a tetra-enamine. The pi-donating tendency of the amine groups strongly modifies the properties of the molecule, which does exhibit properties of a typical alkene.

Reactions
TDAE reacts with oxygen in a chemiluminescent reaction to give tetramethylurea

TDAE is an electron donor with E = 1.06 V vs Fc+/0. It forms a charge transfer salt with buckminsterfullerene:
 * C2(N(CH3)2)4 + C60 → [C2(N(CH3)2)4+][C60−]

Oxidation affords a dication.

Structure
Crystallographic analysis show that TDAE is a highly distorted alkene, the dihedral angle for the two N2C termini is 28°. The C=C distance is alkene-like, 135 pm. The nearly isostructural tetraisopropylethylene also has a C=C distance of 135 pm, but its C6 core is planar. In contrast, [TDAE]2+ is an alkane with multi-C-N bonds.



Synthesis
The reaction of chlorotrifluoroethene and dimethylamine produces TDAE: