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15.5.1.3.1.1.1 Method 1: Protonation/Deuteration

DOI: 10.1055/sos-SD-015-01146

Álvarez, M.; Joule, J. A.Science of Synthesis, (200515744.

A study of the acid-catalyzed exchange in sulfuric acid-d2 at 245°C of the C5- and C8-protons of isoquinoline shows this electrophilic substitution process to involve proton attack at the ring positions of the isoquinolinium cation, e.g. via 306.[‌18‌] This has implications for other reactions of isoquinoline that are conducted in acidic solution. Additionally, iso­quin­oline undergoes exchange at the 1- and 4-positions under these conditions giving tetradeuterated isoquinoline 305, however the rate profiles for these two exchanges are quite different from the electrophilic substitutions at C5 and C8. Exchange at C1 might involve a deuterated salt 307 (Scheme 136); exchange at C4 could involve β-protonation of an enamine-containing covalent hydrate 308.

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