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One of the products obtained from the reaction of ?-diketones with diazomethane is an epoxide1’2’,which under specific conditions is feasible to obtain it as the main product. By treatment of (I) with excess diazomethane in presence of dioxane/benzene (l:1)at-l501L.Mirwa1d3was enabled to obtain the epoxyketone, 10-0 xo-ll-spirodibenzo (a, d) cycloheptadien(1, 4), as the main product. Besides, the treatment of pure epoxyketone with diazomethane yields a small quantity of bisepoxide. B.Eistert and co-workers4 obtained phenanthrenequinone bisepoxide from the reaction of phenanthrenequinone with diazomethane using lithium chloride as a catalyst.
This paper presents the reaction of (I) with diazomethane by using lithium chloride to produce bisepoxide, dibenzo(a,d) cycloheptadien-(1,4)-lO,ll- dispiro-2’,2”-oxirane(II), directly. It appears that this method could be recommended to obtain bisepoxide from ?-diketones.
Moreover,the reaction of(I) with ethyl diazoacetate in presence of a catalyst, such as anhydrous aluminium chloride or anhydrous zinc chloride, produces the l2-carboethoxy-10, ll-dioxo-(dibenzo(a,d)cyclooctadien-(1,4) (III) which is the consequence of the addition of C2H5-C02-CH to compound(I). The structural assignment of (III) was based on elemental analysis and in view of the infrared spectrum. Chemical evidences such as formation of deep red colour with methanolic solution of ferric chloride support the existence of an equilibrium between keto and end form of (III).
The reaction of(I) with ethyldiazoacetat in alcohol in presence of ooppef powder without the addition of anhydrous aluminium or zinc chloride, however, results in formation of product ll-hydroxy-lO-oxo-ll- (ethoxy-ethoxycarbonylmethyl) dibenzo(a,d) cycloheptadien- (1,4), (IV).