Journal of Organic Chemistry p. 1180 - 1185 (1983)
Update date:2022-08-05
Topics:
Carver, David R.
Greenwood, Thomas D.
Hubbard, James S.
Komin, Andrew P.
Sachdeva, Yesh P.
Wolfe, James F.
Photostimulated reactions of 2,6-,2,3-, 3,5-, and 2,5-dihalopyridines (1a-e) with pinacolone potassium enolate (2) in liquid NH3 lead to facile replacement of both halogens via a modified SRN1 mechanism, which does not involve intermediate formation of monosubstitution products.The potassium salts of phenylacetonitrile (12a) and α-ethylphenylacetonitrile (12b) react with 2,6-dibromopyridine (1a) under similar conditions to afford a mixture of mono- and disubstituted products via a related SRN1 process. 4,7-Dichloroquinoline (16) undergoes radical-chain displacement of chloride from C4 with enolate 2. 2,6-Dichloropyrazine (18) and 2,3-dichloropyrazine (20) also undergo monosubstitution with 2 and diisopropyl ketone potassium enolate (22), but these reactions appear to be mainly addition-elimination (SNAr) processes.Treatment of 3,6-dichloropyridazine (27) with 22 results in addition of 22 to C4 of the substrate.Photoassisted reaction of 2,4-dichloropyrimidine (31) with 12a leads to exclusive chloride displacement from C4 via the SRN1 mechanism.
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