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Communication | Regular issue | Vol 20, No. 10, 1983, pp.1959-1962
Published online, 1st January, 1970
DOI: 10.3987/R-1983-10-1959
The Product from the Reaction of Diazomethane with 1,3-Oxaselenole Derived from Dimedone

Katsuhide Matoba and Takao Yamazaki

*Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama, Toyama 930-0194, Japan

Abstract

The 1,3-oxaselenole derivative (VI) obtained from dimedone was treated with an excess of diazomethane to give 1,4,7-dioxaselenocine derivative (VII) in a quantitative yield. The deselenization of VII was carried out by the benzyne-hydrogenolysis method to give 3-methoxy-5,5-dimethyl-2-(5,5-dimethyl-3-oxo-1-cyclohexen-1-yl)oxy-2-cyclohexenone (VIII). Treatment of VII with aqueous alkali gave 5,5,5’,5’-tetramethyl-1,1’,3,3’-tetroxo-2,2’-cyclohexylmethane (IX), and it afforded 4,4-dibromo-3,3-dimethoxy-5,5-dimethylcyclohexanone (X) with bromine in MeOH. VII was reduced spdium borohydride to an allyl alcohol (XIa) which was converted to its acetate (XIb).