The condensation of isoquinolinium salts with aromatic aldehydes

✍ Scribed by E.E. Betts; D.W. Brown; S.F. Dyke; N. Sainsbury

• Publisher: Elsevier Science
• Year: 1966
• Tongue: French
• Weight: 99 KB
• Volume: 7
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)99960-5

✦ Synopsis

1n 1935 Krohnke' reported that benzaldehyde condensed with Z-benzylisoquinolinium bromide (1, R = CHzC9H5), in the presence of alkali, to yield, after acidification with HBr, an alcohol, formulated as (2).

Since it is probable that the pseudobase (3, R = CB2CSH5) is formed from

(1) and the alkali, it seemed to us that a more likely structure for Krohnke's compound is (5, It = CR2CSIi5), formed a8 indicated in (3)j '(4) 4

(51, the pseudobase behaving as an enamine.