38339-46-7

Upstream product

• 876-53-9 1,3-dibromoadamantane 
• 17933-29-8 7-methylenebicyclo[3.3.1]nonan-3-one 

Downstream Products

• 768-95-6 1-adamanthanol 
• 40727-31-9 7-endo-methylbicyclo<3.3.1>nonan-3-one 
• 41189-07-5 7-methylbicyclo<3.3.1>non-6-en-3-endo-ol 
• 189500-02-5 rac-12-amino-6,7,10,11-tetrahydro-9-methyl-7,11-methanocycloocta[b]quinoline 
• 132514-39-7 (R,S)-(1l,2u,3l,5u,7u)-2-(benzyloxy)-7-(dimethoxymethyl)-3,7-dimethylbicyclo<3.3.1>nonane 
• 132514-34-2 (R,S)-(1l,2u,3l,5u)-2-(benzyloxy)-7-(ethylenedioxy)-3-methylbicyclo<3.3.1>nonane 
• 132514-38-6 (R,S)-(1l,2u,3l,5u,7u)-2-(benzyloxy)-7-formyl-3,7-dimethylbicyclo<3.3.1>nonane 
• 132514-36-4 (R,S)-(1l,2u,3l,5u,7l)-2-(benzyloxy)-3-methylbicyclo<3.3.1>nonanespiro-7,2'-1'-oxacyclopropane 
• 132514-35-3 (R,S)-(1l,2u,3l,5u)-2-(benzyloxy)-3-methylbicyclo<3.3.1>nonan-7-one 
• 132514-37-5 (R,S)-(1l,2u,3l,5u,7x)-2-(benzyloxy)-7-formyl-3-methylbicyclo<3.3.1>nonane 
• 905832-15-7 N-p-toluenesulfonyl-3-methyl-1-methoxycarbonyl-2-azaadamantane 
• 905832-17-9 N-p-toluenesulfonyl-1-iodomethyl-3-methyl-2-azaadamantane 
• 905832-16-8 N-p-toluenesulfonyl-1-hydroxymethyl-3-methyl-2-azaadamantane 
• 905832-18-0 N-p-toluenesulfonyl-1,3-dimethyl-2-azaadamantane 

Relevant academic research and scientific papers

HYDROGENATION OF 7-METHYLENEBICYCLONONAN-3-ONE OVER GROUP VIII METAL CATALYSTS. NOVEL REDUCTIVE CYCLIZATION

The products of novel reductive cyclization, 1-adamantanol and 1-methyl-2-oxa-adamantane, were obtained in the hydrogenation of 7-methylenebicyclononan-3-one over group VIII metal black catalysts in ethanol or cyclohexane. 1-Adamantanol was produced over Pd, Rh, Co and Ni catalysts, and 1-methyl-2-oxa-adamantane only over Co catalysts in cyclohexane.

Investigations on Transition-State Geometry in the Aldol Condensation

Model compounds 1 and 2 have been studied to elucidate the relative orientation of enolate and carbonyl moieties in the aldol reaction. The syntheses of these compounds have been achieved from a common precursor derived from fragmentation of adamantane. Models of the limiting transition structures reveal that the cyclization must proceed through either a synclinal or antiperiplanar orientation of the aldehyde with respect to the enolate. Cyclizations of 1 were unexpectedly sluggish due to slow deprotonation of the tertiary center. The cyclization of 2 was very rapid and was studied as a function of enolate type (metal counterion), base type, solvent, and additive. The reactions of metal enolates showed an increasing preference for the syn product 5 with increasing cation coordinating ability (K+ + + +). Attempted cyclization via boron and stannous enolates failed. The type of base and the choice of solvent had negligible effects on the selectivity. However, in the presence of strong cation-complexing agents, the model showed a strong preference for reaction via an antiperiplanar orientation of reactants giving the anti product 6 with high selectivity. The origin of the selectivities and the implication for enolate and transition structures are discussed.