A practicable synthesis of 2,3-disubstituted 1,4-dioxanes bearing a carbonyl functionality from α,β-unsaturated ketones using the Williamson strategy†,10.1039/D0OB01448F

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A practicable synthesis of 2,3-disubstituted 1,4-dioxanes bearing a carbonyl functionality from α,β-unsaturated ketones using the Williamson strategy†

Aramita De,Sougata Santra,Igor A. Khalymbadzha,Adinath Majee

Organic & Biomolecular Chemistry Pub Date : 12/29/2020 00:00:00 , DOI:10.1039/D0OB01448F

Abstract

We have observed that a reagent combination of NaIO₄ and NH₂OH·HCl reacts with α,β-unsaturated ketones followed by the nucleophile ethylene glycol allowing the synthesis of 2,3-disubstituted 1,4-dioxanes using cesium carbonate as a base under Williamson ether synthesis. This reaction is useful for the synthesis of functionalized 1,4-dioxane having a carbonyl functionality. A variety of 2,3-disubstituted 1,4-dioxanes have been synthesized using these reaction conditions. A probable reaction mechanism has also been proposed.