Synthesis of a Water-Soluble Derivative of Cyclohexatriacontane-1,2,13,14,25,26-hexone

Article abstract of DOI:10.1021/jo00367a002

Cyclotrimerization of cyclododecyne and cyclopentadecyne to the corresponding benzene derivatives is catalyzed by Co2(CO)8 and by TiCl3.Ozonolysis of these aromatic compounds, followed by reductive workup and treatment with derivatives of o-phenylenediamine gives in ca. 3percent yield macrocyclic ring compounds: cyclohexatriaconta<1,2,13,14,25,26-b,b',b''>trisquinoxaline (9), cyclohexatriaconta<1,2,13,14,25,26-b,b',b''>tris(1H,3H-2-oxaimidazo<4,5-g>quinoxaline-1,3-di-α-acetate) (17), and cyclopentatetraconta<1,2,16,17,31,32-b,b',b''>trisquinoxaline (10).These compounds do not s hown shape selectivity in facilitated transport of representative hydrocarbons in water.