127106-05-2Relevant academic research and scientific papers
Α-ARYLATION OF ALDEHYDES VIA Α-CHLOROALDIMINES
Kimpe, Norbert De,Zi-Peng, Yao,Schamp, Niceas
, p. 481 - 496 (2007/10/02)
α-Chloroaldimines are arylated at the α-position under Friedel-Crafts conditions via the presumptive intermediacy of α-imidoylcarbenium ions.Aluminium (III)chloride in arenes cleanly converted α-chloro-α-phenylaldimines into α-aryl-α-phenylaldimines.Aliphatic α-chloroaldimines could only be converted into the corresponding α-arylaldimines in low to moderate yields due to a lower reactivity and a competitive side reaction, i.e. dehydrochlorination into 1-aza-1,3-dienes. α-Bromo- and α-iodoaldimines were also evaluated under the given Friedel-Crafts conditions but the results appeared to be negative.The formation of all reaction products (i.e. α-arylaldimines, 1-aza-1,3-dienes and indolines) from the reaction of α-chloroaldimines with arenes in the presence of Lewis acids could be explained by the intermediacy of α-imidoylcarbenium ions, the chemistry of which is discussed to some extent.
