METHOD OF PRODUCING 1,3-DICARBONYL DERIVATIVES OF ADAMANTANES Russian patent published in 2013 - IPC C07C69/753 C07D307/46 C07D295/182 C07C233/58 C07C233/57 C07C61/125 C07C49/84 C07D211/06 

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing 1,3-dicarbonyl derivatives of adamantane of general formula I where R=H, X=OH, OMe, OEt, OPrⁱ, OBu^s, OCH₂CH(Et)Bu, OCH₂CF₃, OCH(CH₃)CF₃, OCH₂CF₂CF₂H, OCH₂CH₂CH₂Br, OCH₂C=CH, NEt₂, NC₅H10 (piperdyl), NC₄H₈O (morpholyl), C₆H₅NH, C₆H₄OMe, C₄H₃O (furyl); R=Me, X-OH, Me, OMe, O-Prⁱ, X=NC₄H₈O (morpholyl), C₄H₃O (furtyl), NEt₂, C₆H₅NH, C₆H₄OMe; involving carbonylation of an adamantane compound in the presence of electrophilic catalysts, where the adamantane compound used is adamantane or 1,3-dimethyladamantane and carbonylation is carried out under the action of CO at atmospheric pressure in a solution of CH₂Br₂ at temperature of 0-25°C for 0.5-3 hours, and the catalyst used is a super-electrophilic CBr₄·2AlBr₃ complex, in molar ratio [CBr₄-2AlBr₃]: [adamantane compound] = (1.5-2):1, and a nucleophilic substrate - water or alcohol - is added to the carbonyl derivative formed in situ, without extraction thereof, in an atmosphere of CO, said substrate containing an alkyl or acetylene or bromoalkyl or polyfluoroalkyl group; or an amine of an aliphatic or heterocyclic or aromatic series; or an aromatic hydrocarbon or an aromatic heterocycle; and reaction with a nucleophile is carried out at temperature of 0-25°C.

EFFECT: single-step method of producing 1,3-dicarbonyl derivatives of adamantanes with two identical carbonyl-containing groups in nodal positions of the adamantane nucleus enables to use readily available adamantane compounds as starting compounds.

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