Unusual reactivity patterns of 1,3,6,8-tetraazatricyclo-[4.4.1.1(3,8)]-dodecane (TATD) towards some reducing agents: synthesis of TMEDA.
نویسندگان
چکیده
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.
منابع مشابه
Crystal structure of the co-crystalline adduct 1,3,6,8-tetraazatricyclo[4.4.1.13,8]dodecane (TATD)–4-bromophenol (1/2)
The structure of the 1:2 co-crystalline adduct C8H16N4·2C6H5BrO, (I), from the solid-state reaction of 1,3,6,8-tetra-aza-tri-cyclo-[4.4.1.1(3,8)]dodecane (TATD) and 4-bromo-phenol, has been determined. The asymmetric unit of the title co-crystalline adduct comprises a half mol-ecule of aminal cage polyamine plus a 4-bromo-phenol mol-ecule. A twofold rotation axis generates the other half of the...
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The asymmetric unit of the title co-crystalline adduct, 1,3,6,8-tetra-aza-tri-cyclo[4.4.1.13,8]dodecane (TATD)-4-iodo-phenol (1/2), C8H16N4·2C6H5IO, comprises a half mol-ecule of the aminal cage polyamine plus a 4-iodo-phenol mol-ecule. A twofold rotation axis generates the other half of the adduct. The components are linked by two inter-molecular O-H⋯N hydrogen bonds. The adducts are further l...
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In the title compound, C19H24N2O2, a di-Mannich base derived from 2-methyl-phenol and 1,3,6,8-tetra-aza-tri-cyclo-[4.4.1.1(3,8)]dodecane, the imidazolidine ring adopts a twist conformation, with a twist about the ring N-C bond [C-N-C-C torsion angle = -44.34 (14)°]. The two 2-hy-droxy-3-methyl-benzyl groups are located in trans positions with respect to the imidazolidine fragment. The structure...
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In the crystal of the title co-crystalline adduct, C8H16N4·C8H9ClO, (I), prepared by solid-state reaction, the mol-ecules are linked by inter-molecular O-H⋯N hydrogen bonds, forming a D motif. The aza-adamantane structure in (I) is slightly distorted, with N-CH2-CH2-N torsion angles of 10.4 (3) and -9.0 (3)°. These values differ slightly from the corresponding torsion angles in the free aminal ...
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BACKGROUND Novel mono N-alkyl quaternary ammonium salts (3a-f) were prepared using the Menschutkin reaction from the cage adamanzane type aminal 1,3,6,8-tetraazatricyclo[4.3.1.13,8]undecane (TATU) and alkyl iodides, such as methyl, ethyl, propyl, butyl, pentyl and hexyl iodide (2a-f), in dry acetonitrile at room temperature. RESULTS The structures of these new quaternary ammonium salts were e...
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ورودعنوان ژورنال:
- Molecules
دوره 12 7 شماره
صفحات -
تاریخ انتشار 2007