�ber den Einflu� von Mangan(II)-chlorid auf die Reaktion zwischen Grignard-Verbindungen und Schiffschen Basen

The Chemistry of Imines.

“…Methylmagnesium iodide reacts with N-isopropylideneaniline (242) to give methane and the a-hydrogen organometallic intermediate CH,(CHtMgI)C=NCaHE,. Marekov and Petsev (173) have recently demonstrated that when N-l-phenylethylideneadhe reacts with isopropylmagnesium chloride propane is liberated and the organometallic product when treated with benzaldehyde or diphenyl ketone gives the a,P-unsaturated imine.…”

“…Both the meso and racemic isomers were isolated (130,131). Isopropylmagnesium chloride reduces N-benzylidenebutylamine in the presence of manganous chloride to give the bimolecular reduction product in 81% yield (242). The bromide gives a 55% yield, while the iodide gives a 44% yield.…”

“…For example, N-benzylidenebutylamine and isopropylmagnesium bromide with 2.5 mole yo of manganous chloride present give a 55% yield of the bimolecular reduction product 1,2-diphenyl-1,2-dianilinoethane, 17% of the addition product, and 5% o€ the reduced product benzylbutylamine. Cobaltous chloride in the same reaction gives the reduced product, benzylbutylamine in 98% yield (242). In the manganous chloride (241) reaction, it was found that the yield of bimolecular reduction product increased in the order: isopropylmagnesium iodide < bromide < chloride.…”