P. Johncock, G. Tudgey, A. Cunliffe
1991
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0
Influential Citations
12
Citations
Journal
Polymer
Abstract
Abstract The reactions of N , N -diglycidylaniline with aniline, 2,6-dimethylaniline, 2,6-dichloroaniline, 2,4,6-trichloroaniline, 3-trifluoromethylaniline and 3,5-bis(trifluoromethyl)aniline were investigated. The formation of similar amounts of the cis (equatorial/equatorial dihydroxy arrangement) and trans (axial/equatorial dihydroxy arrangement) isomers of the eight-membered 3,7-dihydroxy-perhydro-1,5-diazocine ring was the predominant intramolecular cyclization reaction. Steric effects were more important than polar effects in determining the extent of cyclization to the extent that the combined yields of cis and trans isomers was increased from ≈15% with aniline to ≈45% with 2,6-dimethylaniline. Conformational structural assignments were made on the basis of 1 H and 13 C nuclear magnetic resonance spectroscopy and infrared spectroscopy at high dilution.