ChemInform Abstract: Substitution Effect on the Cyclization/Fluorination Reaction of N‐Dienes in Superacid.

Abstract

Superacid. -It is found that the nature of substituents on the nitrogen atom and C=C double bond has strong influence on the outcome of title reaction. Fluorinated pyrrolidines, 3-and 4-fluoropiperidines as well as tetrahydroisoquinolines are available. In some cases, no cyclization takes place. -(VARDELLE, E.; MARTIN-MINGOT, A.; JOUANNETAUD, M.-P.; BACHMANN, C.; MARROT, J.; THIBAUDEAU*, S.; J.

Monofluorination of Organic Compounds: 10 Years of Innovation

“…Many rearrangements can be observed when compounds are treated with HF/SbF 5 . Thibaudeau and co-workers reported rearrangement and fluorination of quinidinone in superacid, and cases of cyclization/fluorination reactions of N -dienes . However, these reactions showed low yields and selectivity.…”