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6816195 
Journal Article 
Selective ejection of anilines from phthalic acid N,N '-substituted diamides under both electron impact and pyrolytic conditions 
Ramana, DV; Yuvaraj, TE; Reddy, KR 
2002 
Yes 
Indian Journal of Heterocyclic Chemistry
ISSN: 0971-1627 
12 
2 
103-108 
WOS:000180371600004 
The ortho interaction between the two anilide functions in N,N'-substituted phthalic acid diamides 1-12 on electron impact leads to the elimination of aniline or substituted amine from the molecular ions, resulting in the formation of W(substituted) phenyl phthalimide or N-phenyl phthalimide radical cations respectively. The presence of electron releasing substituents in the ortho phthalic acid diamides favour the elimination of aniline whereas electron withdrawing substituents in these phthalic acid diamides facilitate the ejection of substituted amine. The mechanisms and ion structures proposed in the mass spectral study are supported by high resolution data and Collision Activated Decomposition-Mass Analyzed Ion Kinetic Energy (CAD-MIKE) spectra. This influence of substituents on selective deamination in phthalic acid N,N'-substituted diamides under electron impact (EI) conditions has been successfully cloned in the laboratory to obtain selectively N-phenyl and N-substituted, phenyl phthalimides in good yields by a pyrolytic approach.