A FACILE EPOXIDATION OF 5-METHYLENE-1,3-DIOXANE-4,6-DIONES WITH HYDROGEN-PEROXIDE WITHOUT CATALYST

Authors
TSUNO T SUGIYAMA K AGO H
Citation
T. Tsuno et al., A FACILE EPOXIDATION OF 5-METHYLENE-1,3-DIOXANE-4,6-DIONES WITH HYDROGEN-PEROXIDE WITHOUT CATALYST, Heterocycles, 38(12), 1994, pp. 2631-2654
Citations number
59
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
38
Issue
12
Year of publication
1994
Pages
2631 - 2654
Database
ISI
SICI code
0385-5414(1994)38:12<2631:AFEO5W>2.0.ZU;2-1
Abstract
5-Methylene-1,3-dioxane-4,6-diones readily reacted with hydrogen perox ide without any catalyst and any bases to afford the spiro- and porysp irocyclic compounds containing an oxirane ring as good crystalline pro ducts. 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 .