Experimental demonstration of anomeric effect and structure: X-ray conformational and configurational analysis of N-2-(1,4-dioxane)-N′-(p-methylbenzenesulfonyl)-O-(p-methylphenoxy) isourea

The conformational, configurational behavior and the structure of N-2-(1,4-dioxane)-N′-(p-methylbenzenesulfonyl)-O-(p-methylphenoxy) isourea () has been studied using X-ray crystallographic analysis. The endo-anomeric effect controls the population of dioxane ring conformers or anomers but not the configuration interconversion of the imine of the imidoyl moiety. X-Ray analysis of demonstrates that the dioxane ring adopts the chair conformation, that the imidoyl amino group prefers axial conformation and that the tosyl and tolyl groups about the CN bond retain the E configuration. Isourea () was synthesized by the thermal decomposition of N′-(p-methylbenzenesulfonyl)-O-(p-methylphenoxy) imidoyl azide in refluxing dioxane.