Ketenimine for Nitrile Rearrangements in N-Arylmethyl Ketenimines: [1,n] Migrations of Bulky Arylmethyl Groups

Title: Ketenimine for Nitrile Rearrangements in N-Arylmethyl Ketenimines: [1,n] Migrations of Bulky Arylmethyl Groups

Volume: 7 Issue: 7

Author(s): Mateo Alajarin, Baltasar Bonillo, Maria-Mar Ortin and Angel Vidal

Affiliation:

Keywords: Ketenimines, nitriles, rearrangements, arylmethyl groups, 2-(azidomethyl)naphthalene, dichloromethane, triphenylphosphine, iminophosphorane, Ketenimine 8, C NMR, mass spectrometry, H NMR, IR analysis, diphenylketene, 2-[2-(2-Naphthyl)methyl]phenyl-2-phenylacetonitrile (10), 2-[4-(9-Anthryl)methyl]phenyl-2-phenylacetonitrile (18)

Abstract: C,C-Diphenyl ketenimines bearing a benzoannulated benzyl group at the nitrogen atom undergo facile 1,3-, 1,5- and 1,7-migrations of the bulky arylmethyl group to the sp2 terminal carbon atom of the ketenimine function and to the ortho and the para positions of one of the C-phenyl substituents.

Cite this article as:

Alajarin Mateo, Bonillo Baltasar, Ortin Maria-Mar and Vidal Angel, Ketenimine for Nitrile Rearrangements in N-Arylmethyl Ketenimines: [1,n] Migrations of Bulky Arylmethyl Groups, Letters in Organic Chemistry 2010; 7 (7) . https://dx.doi.org/10.2174/157017810793362280