Unusual Reactivity Patterns of 1,3,6,8-Tetraazatricyclo-[4.4.1.13,8]-dodecane (TATD) Towards Some Reducing Agents: Synthesis of TMEDA

N,N,N ？,N ？-Tetramethylethylenediamine (TMEDA) can be synthesized by simple reduction of 1,3,6,8-tetraazatricyclo-[4.4.1.1.3,8]dodecane (TATD), an aminal cage type amine, with formic acid. The aminal can be converted to TMEDA in high yield very easily and in a very short time. We comment on the scope and limitations of the reduction of thisaminal and propose a possible reaction mechanism.