ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19670500604
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