Adamantyl-containing fluorinated 1,3-diketones

Chemistry of fluoro-substituted β-diketones and their derivatives

“…C-Adaman-tylation was performed in boiling diethyl ether in dry oxygen-free nitrogen atmosphere with 1.5 ± 2-fold excess of a diketone for 1 ± 2 h, it required no catalyst. 208,209 The reactions of trifluoromethyl-substituted b-diketones 21 with 4,5-dichloro-1,2,3-dithiazolium chloride (Appel's salt, 141) in the presence of pyridine in dichloromethane at room temperature resulted in the corresponding 5-alkylidene-1,2,3-dithiazoles 142 ± 144. 210 In the case of hexafluoroacetylacetone (21b, R = CF 3 ), products 142 and 144 were isolated in the yields of 18% and 44%, respectively.…”

Synthesis of 4-(1-adamantyl)-3-polyfluoromethyl-1H-pyrazoles

“…We previously synthesized a series of adamantylcontaining fluorinated 1,3-diketones Ia-Ie with high yields under mild conditions [8,9]. Structural specificity of such 1,3-diketones is the presence of a strong electron-donor adamantyl group at the α-carbon atom and an electron-withdrawing trifluoromethyl group at one carbonyl carbon atom.…”

1,3-Diketones. Synthesis and properties

“…[54][55][56][57]. Turmasova et al [54] described the alkylation of dicarbonyl compounds with adamantan-1-ol in 1,2-dichloroethane, catalyzed by indium, gallium, scandium, and copper trifluoromethanesulfonates.…”

“…Apart from adamantan-1-ol, 1-chloroand 1-bromoadamantanes were used to alkylate acetylacetone in the presence of iron and manganese acetylacetonates, and the yields of 2-(adamantan-1-yl)pentane-2,4-dione were 75 and 93%, respectively [56]. Dehydroadamantane reacted with fluorinated 1,3-diketones to give 2-(adamantan-1-yl) derivatives in 83-98% yield [57]. The reactions were carried out by…”