Synthesis of N-(Dipheylmethyl)Anilines and P-(Diphenylmethyl)Anilines - Esr Study of Their Photofragmentation (Journal article)

Siskos, M. G./ Garas, S. K./ Zarkadis, A. K./ Bokaris, E. P.

The reaction of N-substituted anilines 2 with diphenylmethyl halides 1 at room temperature in the presence of AlCl3 affords p-substituted derivatives 3 in good yields according to an electrophilic aromatic substitution. In contrast, aniline itself is only converted to the N-substituted compounds 4. A novel rearrangement from Ph3C-NHPh (4c) to p-(triphenylmethyl)aniline (5) is described. Unexpected photofragmentations of 4a, b are studied by using ESR and ENDOR spectroscopy; e.g., irradiation of 4b with quartz- or pyrex-filtered light leads to the formation of the radicals Ph2C-SiMe3 (7b) and Ph2C - NHPh (6) respectively, following selective cleavage of the C - N and C - Si bond.
Institution and School/Department of submitter: Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας
Keywords: benzenamine derivatives, synthesis of,rearrangement, hofmann-martius,diphenylmethyl radicals,esr measurements,endor measurements,single electron-transfer,hindered free-radicals,spin resonance,chemistry,amines,bond,pair
ISSN: 0009-2940
Link: <Go to ISI>://A1992KC74600019
Appears in Collections:Άρθρα σε επιστημονικά περιοδικά ( Ανοικτά)

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