Synthesis of 3-(adamantan-1-yl)pentane-2,4-dione from 1-bromo(chloro, hydroxy)adamantane and acetylacetone in the presence of metal complex catalysts
3-(Adamantan-1-yl)pentane-2,4-dione has been synthesized in high yield by reaction of 1-bromo-, 1-chloro-, or 1-hydroxyadamantane with acetylacetone in the presence of manganese or iron compounds.
Reactions of adamantan-1-ol with β-dicarbonyl compounds in 1,2-dichloroethane in the presence of In(OTf)3, Ga(OTf)3, Sc(OTf)3, or Cu(OTf)2 give the corresponding adamantylated derivatives in 45-93% yields.
Mechanistic studies on the alkylation of pentane-2,4-dione through its Co(II) complex
A mechanistic study on the alkylation of pentane-2,4-dione through its Co(II) complex in concentrated chloroform solutions indicates the operation of a "non carbon radical" chain mechanism based in the ability of cobalt to undergo redox processes between
Vallribera, Adelina,Marquet, Jorge,Moreno-Manas, Marcial,Cayon, Eduard
Synthesis of 1-(2-oxopropyl)adamantane from 1-bromo(chloro)adamantanes and isopropenyl acetate in the presence of iron and manganese compounds
An efficient procedure has been developed for the synthesis of 1-(2-oxopropyl)adamantane by reaction of 1-bromo(chloro)adamantanes with isopropenyl acetate in the presence of manganese and iron compounds.
A DUAL MECHANISTIC PATHWAY IN THE ALKYLATION OF PENTANE-2,4-DIONE THROUGH ITS Co(II) COMPLEX
A mechanistic study on the alkylation of pentane-2,4-dione through its Co(II) complex has shown that a non radical chain mechanism initiated by an electron transfer step induced by Co(II) operates under certain experimental conditions.
Marquet, J.,Moreno-Manas, M.,Pacheco, P.,Vallribera, A.
METAL COMPLEXES IN ORGANIC SYNTHESIS. PREPARATION OF α-(1-ADAMANTYL)-β-DICARBONYL COMPOUNDS AND 4-(1-ADAMANTYL)-3,5-DISUBSTITUTED PYRAZOLES AND ISOXAZOLES.
α-(1-adamantyl)-β-dicarbonyl compounds are prepared by the reactions of the Co(II) complexes of β-dicarbonyl compounds with 1-bromoadamantane.This provides a route to the previously inaccessible 4-(1-adamantyl)-3,5-disubstituted pyrazoles and isoxazoles.
Gonzalez, A.,Marquet, J.,Moreno-Manas, M.
p. 4253 - 4258
(2007/10/02)
ALKYLATION OF β-DIKETONES THROUGH THEIR Co(II), Co(III) AND Zn(II) COMPLEXES. 1-BROMOADAMANTANE AS ALKYLATING AGENT.
α-(1-Adamantyl)-β-diketones are now accessible by the alkylation of Co(II) complexes of β-diketones with 1-bromoadamantane.The intermediacy of adamantyl cation is proposed.Co(II), Co(III) and Zn(II) complexes of pentane-2,4-dione react with alkyl halides precursors of stabilized carbenium ions, to give 3-alkylpentane-2,4-diones.
Gonzalez, A.,Gueell, F.,Marquet, J.,Moreno-Manas, M.
p. 3735 - 3738
(2007/10/02)
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