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Paper | Regular issue | Vol 51, No. 9, 1999, pp.2079-2092
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8583
New 1,3,5-Heterocyclohexanes: Dioxazines, Oxadiazines, Thiadiazines, Oxathiazines and Triazines and Their Amination, Transamination and Disproportionation Reactions

Angelina Flores-Parra* and Sonia A. Sánchez-Ruíz

*Department of Chemistry, Centro de Investigación y de Estudios Avanzados del I.P.N., A.P. 14-740, C.P. 07000 México, D.F., México

Abstract

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.