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 ↗
• View as JSON ↗

Search literature

• Google Scholar ↗
• PubMed ↗
• Wikipedia ↗

More Rearrangement reactions

• 1,2-METALLATE REARRANGEMENT: (Z)-4-(2-PROPENYL)-3-OCTEN-1-OL (3-Octen-1-ol, 4-(2-propenyl)-, (Z)-) Rearrangement
• 1-N-ACYLAMINO-1,3-DIENES FROM 2,4-PENTADIENOIC ACIDS BY THE CURTIUS REARRANGEMENT: BENZYL trans-1,3-BUTADIENE-1-CARBAMATE (Carbamic acid, 1,3-butadienyl-, (E)-, phenylmethyl ester) Rearrangement
• ALKENES via HOFMANN ELIMINATION: USE OF ION-EXCHANGE RESIN FOR PREPARATION OF QUATERNARY AMMONIUM HYDROXIDES: DIPHENYLMETHYL VINYL ETHER (Benzene, 1,1'-[(ethenyloxy)methylene]bis-) Rearrangement
• Allen–Millar–Trippett rearrangement Rearrangement
• Allyl Cyanate-To-Isocyanate Rearrangement: Preparation of tert-Butyl 3,7-dimethylocta-1,6-dien-3-ylcarbamate Rearrangement
• Amadori rearrangement Rearrangement