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1,3-Dehydroadamantane reacted with saturated carboxylic acid chlorides to give the corresponding 1-acyl-3-chloroadmantanes as the major products. In some cases, minor products of insertion into the Cα-H bond of acyl chloride were formed. The reactions of 1,3-dehydroadamantane with aromatic (heteroaromatic) carboxylic acid chlorides selectively afforded aryl (hetaryl) 3-chloroadamantan-1-yl ketones. The described reactions provide a synthetic route to difficultly accessible alkyl (aryl) ketones containing a 3-chloroadamantan- 1-yl group in one step under mild conditions with high yields. [ABSTRACT FROM AUTHOR]

Gas-phase hydrogenation of cycloalkenes in the presence of nickel nanoparticles supported on Ceokar-2, BAU-A activated carbon, alumina, and NaX zeolite proceeds at 140-240°C and atmospheric pressure of hydrogen. The conversion and selectivity depend on the type of support and on the hydrogen excess. [ABSTRACT FROM AUTHOR]

Reaction of 1,3-dehydroadamantane with ethyl esters of α-halocarboxylic acids occurs either at C-H bond, or at C-Hlg bond. The regioselectivity of the reaction depends on the nature of the halogen. The ability of 1,3-dehydroadamantane to react at the C-Hlg grows in the series C-F < C-Cl < C-Br, which correlates with the energies of C-Hlg bonds. Difficultly available 1-R-3-halogen-substituted derivatives of adamantane were prepared under mild conditions in high yields. [ABSTRACT FROM AUTHOR]

Adamantylation of carboxylic acids esters was performed with 1,3-dehydroadamantane for the first time. The reaction proceeds under mild conditions and can be used as a convenient single stage procedure for the synthesis of esters of branched carboxylic acids having an adamantyl group in the α-position to the carbonyl group. [ABSTRACT FROM AUTHOR]

α-Amino nitriles containing a primary amino group undergo transamination with aliphatic and aromatic amines under mild conditions with high yields. A probable reaction mechanism involving intermediate elimination of cyanide ion has been proposed. [ABSTRACT FROM AUTHOR]

A convenient method was developed for the preparation of potentially bioactive substances with 2-adamantyl radical and of intermediates for their synthesis. Condensation of adamantanone with methylene-active compounds was performed, and the reaction features were determined. [ABSTRACT FROM AUTHOR]

Synthetic routes to new amino nitriles with the functional groups at the 2-position of the adamantane core, based on reactions of adamantanonimines with acetone cyanohydrin or of adamantanone cyanohydrin with aliphatic amines, are considered. The products can be used for preparing new biologically active substances, unsymmetrical adamantyl-containing diamines or amino acids. [ABSTRACT FROM AUTHOR]

A convenient and efficient procedure has been developed for the synthesis of 1-azidoadamantane, 1-adamantyl isocyanate, and 1-adamantyl isothiocyanate by reaction of 1,3-dehydroadamantane with hydrazoic, isocyanic, and isothiocyanic acids, respectively, under mild conditions. The reaction of 1,3-dehydroadamantane with hydrogen cyanide under analogous conditions gives adamantane-1-carbonitrile in a poor yield which may be improved using hexane as solvent. [ABSTRACT FROM AUTHOR]

The article presents information on a study conducted on the synthesis of compounds containing nitrogen heterocycles through adamantylation. Such compounds are synthesized through adamantylation of piperidine, piperazine, morpholine with haloadamantanes, or cyclization of difunctional amines. In the study 1,3-Dehydroadamantane was reacted with piperidine, morpholine, and piperazine.

The article focuses on a study regarding the reaction of 1,3-dehydroadamantane with camphor and isocamphanone. The reaction of 1,3-dehydroadamantane (I) with bicyclic ketones including 1,7,7-trimethylbicyclo[2.2.1]- heptan-2-one (II, DL-camphor) and 5,5,6-trimethylbicyclo[ 2.2.1]heptan-2-one isocamphanone was examined. Its reaction with camphor gave approximately equal amounts of two stereoisomeric addition products.

The article discusses the direct noncatalyzed alkylation with 1,3-dehydroadamantane of a series of polycyclic hydrocarbons such as acenaphthylene, tetralin, and fluorene. It results to an isolated adamantylation products purely with the methylene group and not with the aromatic ring for hydrocarbons. It adds that the alkylation with polycyclic hydrocarbon ensures the better selectivity of the monoaddition of the 1,3-dehydroadamantane than at the equimolar reagents ratio.

The article discusses the reaction of 1,3-dehydroadamantane with the compound 3-bromo-1,7,7-trimethylbicycloheptan-2-one. It has been known that the presence of a halogen enhanced the liability of the hydrogen attached to the carbon atom linked to the halogen and it should be facilitate the reaction at the carbon-hydrogen bond. On the other hand, the formation of stereoisomeric compounds was proved by an appearance on a chromatogram of the corresponding peaks with close values of retention time.

and related α-aminonitriles such as (VI) [ABSTRACT FROM AUTHOR]

A letter to the editor is presented which discusses a study on the reactions of 1,3-dehydroadamantane with some aromatic disulfides such as unsymmetrical methyl phenyl disulfide.