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Paper | Regular issue | Vol 57, No. 11, 2002, pp.2107-2114
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9597
Synthesis of Tropocryptands Having Heteroatoms in Linker Chains: A New Class of Macrobicyclic Ligands Derived by N-Acylation and N-Alkylation of Tropocoronand

Ohki Sato, Yutaka Ono, and Josuke Tsunetsugu*

*Department of Chemistry, Faculty of Science, Saitama University, Saitama, Saitama 338-8570, Japan


Tropocoronand (1) reacted with acyl chlorides on endocyclic secondary alkylamines to afford diacyl tropocoronands (2a2c). Double N-acylation of 1 with dioyl dichlorides (3a3d) yielded amide-bridged tropocryptands (4a4d). The similar reactions of 1 with ethylene glycol di-p-tosylate (5) or oligo(ethylene glycol) di-p-tosylate (8a8d) afforded the corresponding tropocryptands (6 or 9a9d).