1972 年 92 巻 12 号 p. 1462-1467
Reaction of the conjugated 1, 2-diimines with isocyanates was investigated. 6, 6', 7, 7'-Tetramethoxy-3, 3', 4, 4'-tetrahydro-1, 1'-biisoquinoline (I) reacted with several phenyl isocyanates (Ila-e) and benzoyl isocyanate (IIf), giving criss-cross type 1 : 2-adducts (IIIa-f). Behavior of N, N'-bis(cyclohexyl)ethylenediimine (VII) was different depending on reaction conditions. Reaction of VII with IIf at room temperature afforded 1 : 2-adduct (VIII) through 1, 2-cycloaddition to C=N bond of VII, presumably due to the contribution of 1, 4-dipolar structure of IIf, while in boiling xylene gave criss-cross type 1 : 2-adduct (X). On the other hand, although addition of N, N'-bis(cyclohexyl)butylene-2, 3-diimine (XV) to IIf was not found to take place at room temperature, XV reacted with IIf in boiling xylene to give a criss-cross adduct (XVI) as VII.