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Favoured conformations of differently N-substituted cis,trans-4,5,6-triphenyl- tetrahydropyrimidin-2(1H)-ones and the allylic strain caused by different groups were studied. It was found that the diequatorial conformer is strongly preferred in equally N,N'-disubstituted products, where the effects of the two substituents negate each other. It was shown that a benzyl group gives rise to much stronger allylic strain than a methyl group. Additionally, unusual azetidine formation was observed upon acid hydrolysis of benzylideneamino azide via S N2 mechanism. It was suggested that N-substitution does not significantly influence the ring geometry angle, while quaternisation affords serious increase of puckering.

Tetrahydropyrimidin-2(1H)-ones with three neighbouring phenyl groups. Synthesis and allylic strain effects