Abstract trans-2-Alkylaminocyclohexanols and trans-2-alkylaminocycloheptanols condense with formaldehyde to give perhydrocycloalkano [d][1, 3] oxazoles, whereas trans-2- alkylaminocyclopentanols give rise to perhydrocyclopentano [f][1, 3, 5] dioxazepines. The two types of ring systems are characterized by differing proton-proton geminal coupling constants and 13 C NMR parameters.