Schönenberger, Helmut and Thies, Heinrich and Rappl, A. (1967) Cytostatic compounds. V. Mechanism of the formation of diphenylethylenediamines from benzylidenealkylamines and activated aluminum. Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft 300 (3), pp. 258-268.
Full text not available from this repository.
cf. CA 63: 16236b; 64: 17599f; 65: 9554e. Redn. of PhCH:NBu with activated Al-Hg in alc. gave a .apprx.3:2 mixt. of dimeric PhCH(NHBu)CH(NHBu)Ph (I) and PhCH2NHBu (II). The I-II ratio was explained by the retention time of the Schiff's base on Al surface. The formation of I requires shorter retention time than that of II. The ratio is dependent upon the basicity of the Schiff's base, and higher temp. favors the formation of I without changing the racemic-meso ratio. The redn. of PhCH:NBu-tert gave the dimeric form exclusively. The dimeric product was also favored by the addn. of a Lewis base, e.g. Et3N. A carbonium-immonium ion mechanism for the redn. is discussed.
|Additional information (public):||CAN 67:21261 22 Physical Organic Chemistry 7429-90-5 Role: RCT (Reactant), RACT (Reactant or reagent) (Schiff base redn. by, mechanism of); 800-13-5P; 3378-72-1P; 3378-81-2P; 16331-79-6P; 16331-80-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)|
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger|
|Keywords:||Reduction (of Schiff bases by activated aluminum, mechanism of) Schiff bases Role: PRP (Properties) (redn. by activated aluminum, mechanism of) REDN DIMERS BENZYLIDENE AMINES BENZYLIDENE AMINES REDN DIMERS AMINES BENZYLIDENE REDN DIMERS|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Unknown|
|Deposited On:||19 Nov 2010 07:28|
|Last Modified:||19 Nov 2010 07:28|