ISSN:
1434-193X
Keywords:
Isoquinolinium N-arylimides
;
Azomethine imines
;
Cycloadditions
;
Heterocycles
;
1,3-Dipoles
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The red isoquinolinium N-arylimides 19-23 are azomethine imines of which the C=N bond is part of an aromatic ring. The N-(4-nitrophenyl)imide 22 and the N-(2-pyridyl)imide 23 were obtained crystalline; in solution the latter equilibrates with the hexahydrotetrazine 24 as its dimer. The N-phenylimide 19 is not stable; an isolated solid appears to be a tetramer. Generated by deprotonation of 11-13, the N-arylimides 19-21 undergo in situ cycloadditions to carbon disulfide, phenyl isocyanate, phenyl isothiocyanate, and diphenylketene. The storable CS2 adduct 29 offers a neutral source of theN-phenylimide 19, since a cycloreversion equilibrium is established in solution.
Type of Medium:
Electronic Resource
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