Unusual reactivity patterns of 1,3,6,8-tetraazatricyclo-[4.4.1.1(3,8)]-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 this aminal and propose a possible reaction mechanism.
Rivera
Augusto
A
Departamento de Química, Universidad Nacional de Colombia, Carrera 30 No. 45-03, Ciudad Universitaria, Bogotá, DC, Colombia. ariverau@unal.edu.co
Rios-Motta
Jaime
J
D000473:Alkanes / Q000737:chemistry*; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry*; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D019163:Reducing Agents / Q000737:chemistry*
C523809:1,3,6,8-tetraazatricyclo(4.4.1.1(3,8))-dodecane; D000473:Alkanes; D006575:Heterocyclic Compounds, 3-Ring; D009942:Organometallic Compounds; D019163:Reducing Agents; C450681:phenyllithium; C007548:n-dodecane