Synthesis of +(1.1.1)>X- Cryptates Assisted by Intramolecular Hydrogen Bonding

Article abstract of DOI:10.1021/jo00219a007

Condensation of <1.1> diazacoronand and diethylene glycol bis(methanesulfonate)as well as with its alkylsubstituted derivatives in the presence of 1 molar equiv of BuLi or KH gives the corresponding +<*>(1.1.1)>X^- cryptates in 31-43percent yields.Experimental results indicate that in the intermediate monosubstituted diazacoronand, the NH hydrogen plays a templating role, thus favoring the bicyclic ring closure by intramolecular hydrogen bonding.Similar base-promoted condensations of <2.1> and <2.2> diazacoronands with triethylene glycol bis(methanesulfonates) afford <2.2.1> and <2.2.2> cryptates in 20-35percent yields.