Thermal Ring-Expansion of N-Acyl Cyclopropyl Imines

Article abstract of DOI:10.1021/jo00082a020

The FVT of N-acyl cyclopropyl imines with methyl, phenyl, and acyl substituents at C-1 or C-2 of the cyclopropyl ring has been studied.The parent N-acyl cyclopropyl imine and N-acyl methylcyclopropyl imines gave no ring-expansion products but ring-opened mixtures, decomposed fragments, and polymerization tars after FVT, whereas N-acyl phenylcyclopropyl imines and N-acyl acylcyclopropyl imines generated ring-expansion products, 2-pyrrolines.It demonstrates the first study on the thermal rearrangement of N-acyl cyclopropyl imines.