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Organic Syntheses via Transition Metal Complexes, 23. - Bicyclic 3-Imidazolines from Primary Isocyanides and Alkenylcarbene Complexes by a Metal-Induced Anomalous Insertion of a C=N-into an α-CH Bond of the Isocyanide
Aumann, Rudolf,Heinen, Heinrich,Krueger, Carl
, p. 1287 - 1292 (2007/10/02)
Alkenylcarbene complexes 1 react smoothly with one equivalent of methyl- and primary isocyanides 2 to give 1:1 adducts 3, which contain C-alkenyl ketenimine ligands.To these a second molecule of 2 may be added in a fashion with formation of bis(imino)cyclopentene complexes 6 or - in a competing reaction path - with induction of a second spontaneous ring closure to 3-imidazoline complexes 4/5 by an insertion of 2 into the α-CH bond of 3.Complexes 4-6 were characterized spectroscopically , the 3-imidazoline complex 4a also by an X-ray analysis.In competition with the addition of 2c to 3c an isomerisation of 3c to the α-alkoxy cyanide complex 9a is observed involving an N/C migration of the N-allyl group.Steric factors exhibit strong influences on the course of the different competition reactions.
