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A method for synthesizing resorcinarene derivatives through dimerization is presented. These derivatives are characterized by self-complementary hydrogen-binding sites and extended sides. Large cavities are observed to form due to the occurrence of dimerization in solvents such as toluene-d8. The thermodynamic parameters for dimerization are believed to have resulted from self-inclusion and hydrogen bonding.

Diisobutylaluminum hydride (DIBAL-H) in the presence of nickel catalyst was found effective in the reductive ring opening of oxabicyclic compounds. It was also observed that phosphine ligands significantly enhances the regioselectivity of the ring opening of bridgehead-substituted oxabicyclic compounds. Deuterium quenching experiments demonstrated the selectivity of the hydroalumination which depends on the reaction protocol and ligand-metal ratio.

A study attempted to furnish a measure of the nitrogen-halogen interactions in an organic solvent through the use of a synthetic cleft-like receptor with affinities ranging from several hundred calories/mole to almost one kcal/mol in benzene. Results show that cleft-like shapes are highly suitable for analyzing weak intermolecular forces as they furnish convergent functional groups. Experimental materials, methodology and findings are discussed.

The coupling reaction between oxobicyclic compounds and organomagnesium halides is discussed. The reaction involves the presence of nickel as catalyst to induce ring-opening of the oxabicyclic compounds. Nickel is suggested to act as the site of the reactions. It allows formation of a metal-pi-allyl complex via oxidative addition to oxabicyclic compounds. The coupling reaction is regioselective and highly stereoselective in which the coupling reaction occurs on one side of the ring.

A new methodology involving a metal-catalyzed hydrometalation-beta-elimination reaction enables selective reductive ring opening of oxabicyclic compounds. Metal catalysts such as nickel enable selectivity modification through introduction of ligands. Triphenylphosphine facilitates the formation of new regioisomers and enhances the regioselectivity of these reactions, which are suitable for asymmetric synthesis of cyclohexenols. The beta-elimination is enhanced by addition of Lewis acids.

Describes the synthesis of resorcinarene derivatives which feature extended sides and self-complementary hydrogen-bonding sites. Factors which influence the cause of dimerization; Characteristics of self-complementary molecules; Conditions under which dimerization occurs.