
%0 Journal Article
%A Wilshire, JFK 
%T The Phthalimidomethyl Rearrangement
%J Australian Journal of Chemistry
%D 1990/11/01
%V 43
%N 11
%P 1817-1826
%K 
%R https://doi.org/10.1071/CH9901817
%U https://www.publish.csiro.au/paper/CH9901817 
%X The discovery of a new acid-catalysed monodentate N &#8594; C aromatic rearrangement, namely the phthalimidomethyl rearrangement, is reported. In this rearrangement, discovered during the reaction of N-hydroxymethylphthalimide with certain alkyl N-(4-nitrophenyl)carbamates in concentrated sulfuric acid solution, the phthalimidomethyl group migrates from its initial location on the nitrogen atom of the carbamate function to a carbon atom of the nitrophenyl group. Evidence, provided by an appropriate 'crossover' experiment, indicates that the rearrangement is intermolecular. Hindered rotation about the N(carbamoyl)-aryl bond of the N-phthalimidomethyl derivatives of both ethyl and methyl N-(2,4-dinitrophenyl)carbamate is reported. 
