Tetrakis(dimethylamino)ethylene (TDAE) is an organic compound with the formula , It is a colorless liquid. It is classified as an enamine. Primary and secondary enamines tend to isomerize, but tertiary enamines are kinetically stable. One unusual feature of TDAE is that it is a tetra-enamine. The pi-donating tendency of the amine groups strongly enhances the basicity of the molecule, which does exhibit properties of a typical alkene.
TDAE reacts with oxygen in a chemiluminescent reaction to give tetramethylurea. The initial intermediate is (2+2) adduct, a 1,2-dioxetane. This species decomposes to electronically excited tetramethylurea. This returns to the ground state is accompanied by emission of green light with a maximum at 515 nm.
TDAE is an electron donor with E = 1.06 V vs Fc<sup>+/0</sup>.
TDAE has been examined as a reductant in coupling reactions.
As one of many of examples of its redox behavior forms a charge-transfer salt with buckminsterfullerene:
Oxidation affords a dication.
Crystallographic analysis show that TDAE is a highly distorted alkene, the dihedral angle for the two N2C ends is 28ð. 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]<sup>2+</sup> is an alkane with multi-C-N bonds.
It is available by pyrolysis of tris(dimethylamino)methane by pyrolysis or from chlorotrifluoroethene and dimethylamine.