Chemical mechanistic investigation demonstrates 40% methylene rearrangement during nitrous acid deamination, highlighting carbocation pathway dynamics.
The synthesis of 2-[p-(2'-hydroxyethoxy)phenyl]ethylamine (I) and the subsequent aqueous acid deamination has been carried out and the major products identified. The deuterium- labeled amine (Ia) has been similarly deaminated and the extent of rearrangement of the methylene groups has been determined to be 40% by means of nuclear magnetic resonance spectroscopy. See PDF abstract for figures.
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Robert David Levin (2026) studied this question.
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