Intramolecular Hydrogen Bonding-Promoted Formation of Macrocycles: Dynamical and Thermodynamic Control Approaches

doi:10.6023/cjoc201207034

Abstract

Hydrogen bonding-induced aromatic amide oligomers may adopt folded, helical, extended or zigzag conformations. This feature of structural preorganization can be utilized to promote the formation of macrocycles. When reactive groups are introduced at the ends of the aromatic amide backbones, the preorganization of the backbones may induce them to adopt discrete required spatial orientations. When macrocyclization concerns the formation of irreversible covalent, carbon-metal and coordination bonds, preorganization may facilitate the formation of specifically designed macrocycles. When macrocyclization involves the formation of reversible covalent bonds such as imine and hydrazone, rationally designed macrocycles may be produced in high or even quantitative yields after the reactions achieve equilibrium and are controlled thermodynamically.

Key words: hydrogen bonding, macrocycle, aromatic amide, imine, dynamically controlled reaction, thermodynamically controlled reaction

Cite this article

Zhang Danwei, Li Zhanting. Intramolecular Hydrogen Bonding-Promoted Formation of Macrocycles: Dynamical and Thermodynamic Control Approaches[J]. Chin. J. Org. Chem., 2012, 32(11): 2009-2017.

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