1,3-DICARBONYL DERIVATIVES OF ADAMANTANES AND PRODUCTION METHOD THEREOF Russian patent published in 2012 - IPC C07C69/753 C07D307/46 C07D295/182 C07C233/58 C07C233/57 C07C61/125 C07C49/84 

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing 1,3-dicarbonyl derivatives of adamantane of general formula , where R = H, X = OCH(CH₃)CF₃, OCH₂CF₂CF₂H, OCH₂CH₂CH₂Br, C₄H₃O (furyl); OH, OMe, OEt, OPrⁱ, OBu^s, OCH₂CF₃, OCH₂C=CH, NEt₂, NC₄H₈O (morpholyl), NHC₆H₅, C₆H₄OMe; R = Me, X = Oprⁱ, NC₄H₈O (morpholyl), C₄H₃O (furyl), NEt₂, NHC₆H₅; OH, OMe, C₆H₄OMe, involving carbonylation of an adamantane compound in the presence of electrophilic catalysts, the adamantane compound used being 1-bromadamantane or 1,3-dimethyl-5-bromadamantane and carbonylation is carried out with CO at atmospheric pressure in a CH₂Br₂ solution at temperature 0-25°C for 0.5-3 hours, and the catalyst used is a CBr₄•2AlBr₃ superelectrophilic complex, with molar ratio [CBr₄•2AlBr₃] : [adamantane compound] = (1.2-1.5):1, and a nucleophilic substrate is added to the carbonyl derivative formed in situ without separation thereof in a CO atmosphere, said nucleophilic substrate being water or aliphatic alcohol selected from MeOH, EtOH, i-PrOH, sec-BuOH, fluorine- or bromine-containing alcohol, or an alcohol containing an acetylene group selected from CF₃CH₂OH, HOCH(CH₃)CF₃, HOCH₂CF₂CF₂H, HOCH₂CH₂CH₂Br, HOCH₂C=CH; an aliphatic, cyclic or aromatic amine selected from diethylamine, morpholine, aniline; an aromatic or heteroaromatic hydrocarbon selected from anisole, furan; and the reaction with the nucleophile is carried out at temperature from 0°C to 25°C.

EFFECT: use of the disclosed method enables to obtain end products with high output and high selectivity in a single step in mild conditions.

23 ex