New 1,3,5-heterocyclohexanes: Dioxazines, oxadiazines, thiadiazines, oxathiazines and triazines and their amination, transamination and disproportionation reactions

Article abstract of DOI:10.3987/COM-99-8583

New 1,3,5-heterocyclohexanes: 5-alkyl-1,3,5-dioxazines (R= iPr, tBu and [R]-α-methylbenzyl), 3,5-di([R]-α-methylbenzyl)-1,3,5-oxadiazine, 3,5- di([R]-α-methylbenzyl)-1,3,5-thiadiazine, 5-isopropyl-1,3,5-oxathiazine, 1- isopropyl-3,5-dimethyl-1,3,5-triazine, 1-tert-butyl-3,5-dimethyl-1,3,5- triazine are reported. Amination and transamination reactions of 1,3,5- heterocyclohexanes were investigated. Equilibria between different heterocycles were found. ¹³C NMR studies allowed to observe new 1,3,5- heterocycles: 1,3,5-triazines bearing two different alkyl substituents, 3,5- ditert-butyl-1,3,5-thiadiazine, 3-tert-butyl-5-isopropyl-1,3,5-oxadiazine. 1,3,5-heterocyclohexanes present a ring fluxional behavior, the ring inversion energy was calculated for dioxazines, oxadiazine, thiadiazines and triazines.