The Phthalimidomethyl Rearrangement

1990 ◽  
Vol 43 (11) ◽  
pp. 1817 ◽  
Author(s):  
JFK Wilshire

The discovery of a new acid-catalysed monodentate N → 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.


2000 ◽  
Vol 64 (5) ◽  
pp. 367-370
Author(s):  
Hideyuki Ogishi ◽  
Takeshi Suemitsu ◽  
Akira Takashima ◽  
Hyoe Ono ◽  
Hidemi Ukai ◽  
...  


2006 ◽  
Vol 45 (No. 14) ◽  
pp. L406-L408 ◽  
Author(s):  
Hideki Masuda ◽  
Mitsutaka Nagae ◽  
Takuya Morikawa ◽  
Kazuyuki Nishio


1985 ◽  
Vol 63 (7) ◽  
pp. 2081-2085 ◽  
Author(s):  
J. W. Lewis ◽  
R. V. Nauman

The ambient temperature ultraviolet absorption and the 77 K luminescence spectra of a series of four hydrocarbon derivatives of azulene in sulfuric acid solution are presented and discussed in detail. CNDO/S calculations have been carried out and the calculational results are compared with the experimental results. The phosphorescences of these cationic species are reported for the first time. The present results suggest that an inversion in the order of electronic states is perhaps responsible for the normal emissions of the protonated species and the anomalous emissions of the parent molecules.



1989 ◽  
Vol 173 ◽  
Author(s):  
Xian-Tong Bi ◽  
C. Wang ◽  
J. S. Bao

ABSTRACTThe improvement of the processibility and mechanical properties of poly-aniline (PAn) by processing a concentrated sulfuric acid solution of the mixture of chemically prepared conductive PAn powders and poly(p-phenylene-terephthalamide) (PPTA) in different weight ratios are presented.The concentrated sulfuric acid solution of PAn and PPTA were processed to films and threads, they are liquid crystalline conductive polymer composites, the electrical conductivities of the composites are between 10−4 -10−1 s/cm.PAn enhanced the tensile strength of PPTA, but does not effect the elongation. The morphology of the PPTA/PAn composite surfaces are fiberlike texture.







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