SYNTHESES OF AROMATIC BRIDGED CRYPTOPHANES AND THEIR COMPLEXING ABILITIES WITH ALKYL AMMONIUM CATIONS

Several aromatic bridged cryptophanes were successfully synthesized. p -Xylene bridged cryptophane Anti-3 was prepared by the direct trimeriz ation of a'-bis[4-hydroxymethyl-2-methoxyphenoxy]-p-xylene. The synthe sis of o-xylene bridged cryptophane Anti-8 was carried out by the dire ct trimerization and/or the stepwise method from vanillyl alcohol. The o-[4,5-bis(methoxycarbonyl)]xylene bridged cryptophanes Anti-15a and Syn-15b were also prepared by the stepwise method from vanillyl alcoho l. Anti-3 was capable of complexing with almost all the quaternary alk ylammonium cations among the primary, secondary, tertiary and quaterna ry ammonium cations, and selectively prefered to complex with the NEt( 3)Me(+) cation as a guest. From the complexation of the o-xylene bridg ed cryptophanes Anti-8, and the analogs Anti-15a and Syn-15b with the NMe(4)(+) cation, the cryptophanes Anti-8 and Syn-15b were confirmed t o complex with the guest cation, however, Anti-15a was not confirmed t o be included.