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Paper | Regular issue | Vol 38, No. 12, 1994, pp.2631-2654
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6865
A Facile Epoxidation of 5-Methylene-1,3-dioxane-4,6-diones with Hydrogen Peroxide without Catalyst

Takashi Tsuno,* Kunio Sugiyama, and Hideo Ago

*College of Industrial Technology, Nihon University, 1-2-1, Izumi-cho, Narashino, Chiba 275-8575, Japan

Abstract

5-Methylene-1,3-dioxane-4,6-diones readily reacted with hydrogen peroxide without any catalyst and any bases to afford the spiro- and poryspirocyclic compounds containing an oxirane ring as crystalline products. Furthermore, the epoxidation of chiral 5-arylidene-1,3-dioxane-4,6-diones with hydrogen peroxide produced the two diastereomers whose purification by silica gel chromatography ensures 100% optical purity.