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

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

Journal Name: Letters in Organic Chemistry

Volume 7 , Issue 7 , 2010

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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.

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)

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Article Details

VOLUME: 7
ISSUE: 7
Year: 2010
Page: [528 - 532]
Pages: 5
DOI: 10.2174/157017810793362280
Price: $65

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