Nucleophilic Displacement Reactions of Hexachlorocyclopentadiene II
Reactions with secondary amines
In a continued study of reactions undergone by hexachlorocyclopentadiene with nucleophiles, the halide was treated with secondary aliphatic amines to give 5,5-diamino-1,2,3,4-tetrachlorocyclopentadienes. Allyl alcohol reacted with 5,5-dimorpholinyl-1,2,3,4-tetrachlorocyclopentadiene to give 5,7-methyleneoxy-7-morpholinyl-1,2,3,4-tetrachlorobicyclo[2.2.1]-hept-2-ene, an intramolecular Diels-Alder adduct, which on hydrolysis produced exo-5-hydroxymethyl-1,2,3,4-tetrachlorobicyclo[2.2.1]hept-2-en-7-one.
E. T. McBee et al., "Nucleophilic Displacement Reactions of Hexachlorocyclopentadiene II," Journal of the American Chemical Society, American Chemical Society (ACS), Jan 1962.
The definitive version is available at http://dx.doi.org/10.1021/ja00882a033
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© 1962 American Chemical Society (ACS), All rights reserved.