The N-cyclopropylimine-1-pyrroline photorearrangement as a synthetic tool: scope and limitations.
The scope and limitations of the photorearrangement of N-cyclopropylimines to 1-pyrrolines are presented. The influence on the reactivity of different substituents throughout the cyclopropane ring and at the iminic position of the N-cyclopropylimine structure is discussed. The observed effects are interpreted from computational studies. The principal findings relate to (1) the enhanced reactivity of 1-substituted compounds toward rearrangement, (2) the lack of reactivity of crowded cyclopropanes, and (3) the high chemoselectivity of the process.
Soldevilla
Alberto
A
Departamento de Química, Universidad de La Rioja, Grupo de Síntesis Química de La Rioja, Unidad Asociada al CSIC, Madre de Dios 51, E-26006 Logroño, Spain.
Sampedro
Diego
D
Campos
Pedro J
PJ
Rodríguez
Miguel A
MA
D009682:Magnetic Resonance Spectroscopy; D010777:Photochemistry; D011758:Pyrroles / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
C510910:N-cyclopropylimine-1-pyrroline; D011758:Pyrroles