ChemInform Abstract: Photo-Emde Degradation of 1,2,3,4-Tetrahydroquinolinium Salts.
Abstract
In order to corroborate the proposed mechanism of (I)- (IVa) via the intermediate (IIIa), the photochemical (direct irradiation through quartz) cleavage of the N - Cbond in quinolinium salts (III) is examined (named "photo-emde degradation" in analogy to the Emde degradation reaction using Na - Hg).
ChemInform Abstract
In order to corroborate the proposed mechanism of (I)- (IVa) via the intermediate (IIIa), the photochemical (direct irradiation through quartz) cleavage of the N - Cbond in quinolinium salts (III) is examined (named "photo-emde degradation" in analogy to the Emde degradation reaction using Na - Hg). The ring-opened products (IV) [loss of C1 in the case of (IIIg)] are obtained in reasonable yields; the fact that 28 (IIIf) is only deuterated in [D4lmethanol [- (V)] suggests a reaction pathway involving the homolytic scission of the C - Nbond with formation of a phenyl radical.
