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Reaction of certain isocyanates with azomethines. Evidence for a new heterocyclic adduct
Author(s) -
Chupp John P.,
Landwehr Helen K.
Publication year - 1968
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570050210
Subject(s) - chemistry , chlorobenzene , isocyanate , adduct , stoichiometry , ring (chemistry) , polymer chemistry , catalysis , alkyl , elemental analysis , benzene , organic chemistry , polyurethane
The preparation of triazinone (I) from certain isocyanates and N ‐alkyl azomethines was found to proceed easily without catalyst, particularly in refluxing chlorobenzene. The physical and chemical properties, including n.m.r. spectra of the oily triazinones, are contrasted with the newly discovered solid adducts arising from low temperature reaction of azomethine and chlorophenyl isocyanates. From stoichiometry of the reaction, elemental analysis, molecular weight of the products, and spectral analyses, the new materials (II) were found to incorporate two isocyanate and three azomethine moieties in their molecular make‐up. The relative merits are considered for assigning II a molecular structure arising from a complex between a four and six‐membered ring (III, IV) versus a ten‐membered ring system (V, VI, VIa).