Thies, H. and Schönenberger, Helmut and Zeller, A. (1965) Reactions of Schiff bases. XI. Effect of heavy metal halides on the reaction between Grignard-type compounds and Schiff bases. Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft 298 (1), pp. 26-33.
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cf. CA 54, 18432c; 55, 18634c; 56, 363a. The reaction between benzylidenebutylamine (I) with the Grignard reagent iso-PrMgBr2 was used as model reaction to study the influence of heavy metal halides on products and yield. Without any metal halide addn., the reaction products were chiefly alpha -phenyl-alpha -butylamino-beta -methylpropane (II) and some benzylbutylamine (III) as a monomeric redn. by-product. Formation of the dimeric N,N'-dibutyl-alpha ,alpha '-diphenylethylenediamine (IV) did not take place under these reaction conditions. The presence of metal chlorides had the following influence on the reaction products: Co2+, Fe2+, and Ni2+ increased formation of III, Mn2+ andTi3+ enhanced formation of IV, and Cr3+ increased the yield of both III and IV. In all cases was the yield of II reduced correspondingly. Many chlorides such as CoCl2 and MnCl2 markedly increased also the reaction rate. Without much influence on the reaction products were the chlorides of Ca, Al, Pb2+, Cu, Zn, Hg2+, and V3+. It was further demonstrated that also the halide used in prepg. the Grignard reagent affected the reaction. The yields of II in the reaction of I with Grignard reagents contg. various halides increased always in the order I < Br < Cl.
|Additional information (public):||CAN 62:74285 39 Organometallic and Organometalloidal Compounds 4169-62-4; 6867-97-6 (Derived from data in the 7th Collective Formula Index (1962-1966); 7439-95-4 (Magnesium) (compds., alkyl halo, reaction with alkyl halides, catalysts and); 1137-52-6P (Benzylamine, N-butyl-alpha -isopropyl-); 2403-22-7P (Benzylamine, N-butyl-) Role: PREP (Preparation) (formation from N-benzylidenebutylamine and isopropylmagnesium halides); 1165-52-2P (Ethylenediamine, N,N'-dibutyl-1,2-diphenyl-, meso-) Role: PREP (Preparation) (formation in N-benzylidenebutylamine reaction with isopropylmagnesium halides); 109-73-9P (Butylamine) Role: PREP (Preparation) (formation of, in N-benzylidenebutylamine reaction with isopropylmagnesium halides); 7705-07-9 (Titanium chloride, TiCl3) (in N-benzylidenebutylamine reaction with isopropylmagnesium halides); 1077-18-5 (Butylamine, N-benzylidene-) (reaction with isopropylmagnesium halides in presence of transition metal halides); 920-39-8 (Magnesium, bromoisopropyl-); 1068-55-9 (Magnesium, chloroisopropyl-); 1068-56-0 (Magnesium, iodoisopropyl-) (reaction with N-benzylidenebutylamine in presence of transition metal halides); 7446-70-0 (Aluminum chloride); 7447-39-4 (Copper chloride, CuCl2); 7487-94-7 (Mercury chloride, HgCl2); 7646-79-9 (Cobalt chloride, CoCl2); 7646-85-7 (Zinc chloride); 7705-08-0 (Iron chloride, FeCl3); 7718-54-9 (Nickel chloride, NiCl2); 7718-98-1 (Vanadium chloride, VCl3); 7758-95-4 (Lead chloride, PbCl2); 7773-01-5 (Manganese chloride, MnCl2); 10025-73-7 (Chromium chloride, CrCl3); 10043-52-4 (Calcium chloride) (N-benzylidenebutylamine reaction with isopropylmagnesium halides in presence of)|
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger|
|Keywords:||Schiff bases (Grignard reaction of, in presence of transition metal halides) Transition metal halides (Grignard reaction with Schiff bases in presence of) Grignard reaction (with Schiff bases in presence of transition metal halides)|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Unknown|
|Deposited On:||18 Nov 2010 11:09|
|Last Modified:||18 Nov 2010 11:13|