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Isoquinolinium N ‐Arylimides and Some Cycloadditions to Heterocumulenes
Author(s) -
Bast Klaus,
Behrens Matthias,
Durst Toni,
Grashey Rudolf,
Huisgen Rolf,
Schiffer Reinhard,
Temme Robert
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199802)1998:2<379::aid-ejoc379>3.0.co;2-f
Subject(s) - chemistry , phenyl isothiocyanate , imide , deprotonation , dimer , adduct , tetramer , isocyanate , ring (chemistry) , isothiocyanate , medicinal chemistry , heteroatom , cycloaddition , polymer chemistry , organic chemistry , catalysis , ion , polyurethane , enzyme
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 CS 2 adduct 29 offers a neutral source of the N ‐phenylimide 19 , since a cycloreversion equilibrium is established in solution.