SYNTHETIC AND MECHANISTIC ASPECTS OF THE COURSE OF THE COLOR-REACTIONOF IMINODIBENZYL WITH ARYL-ALDEHYDE OR HETARYL-ALDEHYDE - AN ACCESS TO NEW HETARYL- ARYL-METHANES AND 4,5-DIAMINO-CYCLOPENTENONES/

The analytical colour reaction of iminodibenzyl with hetaryl/aryl alde hydes, was studied in detail to clarify the mechanism of the reaction path. On the basis of synthetic and structural analytical investigatio ns iminodibenzyl-aryl/hetaryl-carbenium ions were found to be the deci sive products responsible for the colour reaction. In order to analyse the scope and limitations of this aromatic electrophilic substitution reaction some related aniline derivatives with different nucleophilic ity were also investigated by reaction with furan-2-carbaldehyde. In t his context new 4,5-diamino-2-cyclopenten-1-ones were formed and chara cterized which gave rise to valuable structural information concerning the aniline/furan-2-carbaldehyde colour reaction frequently used in t he analytical chemistry of aminoglycoside antibiotics.