A new application about N1-(2-(Dimethylamino)ethyl)-N1,N2,N2-trimethylethane-1,2-diamine

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Metal-Induced C-N Bond Cleavage in the Decomposition of Alkali (R,R)-Bis(alpha-methylbenzyl)amide Complexes

This study resulted in the isolation of new alkali metal complexes of (R,R)-bis(alpha-methylbenzyl)amine (B-alpha-mba) characterized by NMR spectroscopy and single-crystal X-ray diffraction where possible. The reaction outcome was found to be dependent on metal and Lewis donor choice to afford species [{PhCH(CH3)}2NLi¡¤Dioxane]2 2, [{PhCH(CH3)}2NLi¡¤HMPA]2 3, [{PhCH(CH3)}2NLi¡¤TMEDA] 4, and [{PhCH(CH3)}2NNa¡¤(THF)k]n 5 as simple amido species. Complex [{PhC(-CH2)}{PhCH(CH3)}NNa¡¤TMEDA]? 6 was isolated as a result of a beta-hydride elimination. A complex mixture of species was isolated when B-alpha-mba was reacted with potassium in the presence of TMEDA and PMDETA to give species [{PhCH(CH3)}2NK¡¤(TMEDA)k]n 7a, [{PhC(-CH2)}{PhCH(CH3)}NK¡¤(TMEDA)k]n 7b, [{PhC(-CH2)NH}K¡¤(TMEDA)k]n 7c, [{PhCH(CH3)}2NK¡¤(PMDETA)k]n 8a, [{PhC(-CH2)}{PhCH(CH3)}NK¡¤(PMDETA)k]n 8b, and [{PhC(-CH2)NH}K¡¤(PMDETA)k]n 8c. In both cases, the decomposition to form the potassium enamide species 7c and 8c was the more favorable process. The decomposition reaction of B-alpha-mba with nBuNa in the presence of PMDETA to give the sodium enamide [PhC(-CH2)N(H)Na¡¤PMDETA] 1 was investigated with GC-MS studies revealing the byproduct of this decomposition as styrene.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI