Unusual reactivity patterns of 1,3,6,8-tetraazatricyclo-[4.4.1.1 3,8]-dodecane (TATD) towards some reducing agents: Synthesis of TMEDA

Abstract

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 this aminal and propose a possible reaction mechanism. © 2007 by MDPI.