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Isochinoline. 1. Mitteilung. Über die Umlagerung von α, α‐Dialkylhomophtalimiden zu Derivaten des 1‐Chlor‐3, 4‐dialkyl‐isochinolins
Author(s) -
Marquardt F.H.,
Nair M. D.
Publication year - 1967
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19670500604
Subject(s) - chemistry , isoquinoline , disproportionation , medicinal chemistry , derivative (finance) , protonation , stereochemistry , organic chemistry , catalysis , ion , financial economics , economics
On reinvestigation of the reaction of wet phosphorus oxychloride with α,α‐dimethylhomophthalimide, 1‐chloro‐3‐chloromethyl‐4‐methyl‐isoquinoline and 1‐chloro‐4‐chloromethyl‐3‐methyl‐isoquinoline were isolated as the main products (aside from some substances resulting from a redox disproportionation). The production of these two substances can be rationalized by assuming a mechanism in which the rearrangement product is a protonated derivative of 3,4‐dimethylene‐3, 4‐dihydroisoquinoline. With α, α‐diethyl‐homophthalimide the only isolated product was a derivative of 1‐chloro‐3, 4‐diethyl‐isoquinoline, with a chlorine atom in β‐position of one of the ethyl groups, while with α‐methyl‐α‐benzyl‐homophthalimide the isolated product was 1,3‐dichloro‐4‐methyl‐isoquinoline, i.e. elimination had taken place instead of rearrangement. Also these results are in agreement with the proposed mechanism.