J. Zoltewicz, Terence M. Oestreich
Apr 1, 1991
Citations
0
Influential Citations
6
Citations
Journal
Journal of Organic Chemistry
Abstract
4-Bromo- or 4-chloroisoquinoline in refluxing liquid ammonia containing amide and thiomethoxide ions reacts preferentially with the thiolate ion to give 4-(methylthio)isoquinoline in high yield. The bromo substrate was shown to require amide ion in order to react with thiomethoxide ion, no reaction taking place in its absence. Substitution product is believed to form from both halides by an S RN 1 mechanism. By contrast, 3-chloroisoquinoline under the same conditions of mixed anions gives 3-aminoisoquinoline. The role of amide ion and its addition to give σ complexes in these and other reactions of 4-halogenated isoquinolines in ammonia is discussed