Orthocyclophanes. 2. Starands, a New Family of Macrocycles of Spirobicyclic Polyketals with a 2n-Crown-n Moiety

Article abstract of DOI:10.1021/jo00077a044

Synthesis and functionalization of higher members of the <1_n>orthocyclophanes, or <1_n>OCPs, have been investigated.Oxidation of the benzylic methylenes in <1_n>OCPs gave the polyoxo derivatives.Exhaustive oxidation of all methylenes in even-numbered <1_n>OCPs gave rearranged isomers of the cyclopolyketal structure instead of the corresponding polyoxo derivatives.We propose the class name "starands" for this new family of crown compounds for their star-shaped crown ether structure.Detailed synthesis and characterization of two starands are described.