ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
It is shown that 1,1-dimethyl-1,2,3,4-tetrahydroquinolinium ions undergo, under direct irradiation through quartz in CH3OH and independent of the nature of the counterion (I-, BF4-), a reductive cleavage of the N(1)-C(8a) bond (photo-Emde degradation). The corresponding N,N-dimethyl-3-phenylpropylamines are formed in high yields and without contamination by Hofmann degradation products of the tetrahydroquinolinium salts. Me groups at C(2) as well as substituents at C(6) (CH3, Cl, CH3O) favour the photo-Emde degradation. The aromatic Cl-substituent is reductively split off in the course of the photoreaction.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19850680721
