Aromatic compounds

Model
Digital Document
Publisher
Florida Atlantic University
Description
In this research it was found that strongly
nucleophilic aromatic compounds, like phenol, resorcinol,
anisole, N,N-dimethylaniline, mes.l.tylene, thiophene,
thianaphthene, N-methylpyrrole, indole and ferrocene, are
ferrocenylmethylated on a ring-carbon by (ferrocenylmethyl)-
trimethylammonium iodide. The ferrocenylmethylation of aniline, N-methylaniline
and acetanilide yielded N-, o- and p-ferrocenylmethylated
products. The N-ferrocenylmethylated compounds have been
shown to undergo acid catalyzed intermolecular rearrangements
to their corresponding o- and p-ferrocenylmethyl
isomers. NMR was especially useful in structure analysis.