Weakening of amide conjugation with a nitrogen atom included in a four-membered ring

The barriers to amide rotation about the N-N bond in 1-nitrosoazetidine, dimethylnitrosamine, 1-formylazetidine, 1,1-carbonylbisazetidine, 1-dimethylcarbamoylazetidine, and dimethylformamide were measured by dynamic NMR spectroscopy. 1,1-Carbonylbisazetidine and 1-dimethylcarbamoylazetidine, the structures of which were confirmed by data from the PMR and ¹³C NMR spectra, were obtained.Translated from Khimiya Geterotsiklicheskikh Soedenenii, No. 7, pp. 912–194, July, 1987.