
TY  - JOUR
A1  - Wilshire, JFK 
T1  - The Phthalimidomethyl Rearrangement
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1990
VL  - 43
IS  - 11
SP  - 1817
EP  - 1826
KW  - 
UR  - https://doi.org/10.1071/CH9901817 
N2  - 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. 
ER  -

