Hofmann–Löffler reaction

Overview

In organic chemistry, the Hofmann–Löffler reaction (also referred to as Hofmann–Löffler–Freytag reaction, Löffler–Freytag reaction, Löffler–Hofmann reaction, as well as Löffler's method) is a radical amine cyclization, forming a 5- (or in rare cases, 6-) membered ring. In the reaction, thermal or photochemical decomposition of N-halogenated amine 1 in the presence of a strong acid (concentrated sulfuric acid or concentrated CF3CO2H) generates a nitrogen radical intermediate. The radical then abstracts an intramolecular hydrogen atom to give a cyclic amine 2 (pyrrolidine or, in some cases, piperidine).

Actions

• This entry doesn't have stoichiometric equivalents on file yet — the Reaction Scale Calculator needs at least one participant tagged with an equivalents value.
• Mechanism / source ↗