76241-07-1Relevant academic research and scientific papers
Synthesis of N- and p-(Diphenylmethyl)anilines. ESR Study of their Photofragmentation
Siskos, Michael G.,Garas, Stylianos K.,Zarkadis, Antonios K.,Bokaris, Efthymios P.
, p. 2477 - 2482 (2007/10/02)
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.Key Words: Benzenamine derivatives, synthesis of / Rearrangement, Hofmann-Martius / Diphenylmethyl radicals / ESR measurements / ENDOR measurements
