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- Title
Synthesis and Properties of First Bis(fluoreno)crownophanes.
- Authors
Lyapunov, A.; Kirichenko, T.; Kulygina, E.; Luk’yanenko, N.
- Abstract
Alkylation of 2,7-dihydroxy-9 H-fluoren-9-one with 2-(2-chloroethoxy)ethanol, 2-[2-(2-chloroethoxy)-ethoxy]ethanol, and 2-{2-[2-(2-chloroethoxy)ethoxy]ethoxy}ethanol in dimethylformamide in the presence of potassium carbonate gave 78–80% of the corresponding diols which were treated with p-toluenesulfonyl chloride in a dioxanechloroform mixture in the presence of triethylamine at 0– 5°C (30 h). The resulting bis( p-toluene-sulfonates) were brought into condensation with 2,7-dihydroxy-9 H-fluoren-9-one in a very dilute solution in dimethylformamide containing anhydrous potassium carbonate at 80–85°C. Appropriate treatment of the reaction mixture, followed by chromatographic purification afforded 53–27% of the first representatives of a new class of cyclophanes, bis(oxofluoreno)crownophanes. Raising the temperature to 95–105°C resulted in an appreciable decrease of the product yield. The yield of the target products did not increase on replacement of potassium carbonate by cesium carbonate.
- Subjects
FLUORENE; ALKYLATION; ALCOHOL; DIMETHYLFORMAMIDE; POTASSIUM; CHEMICAL reactions; CONDENSATION; CHROMATOGRAPHIC analysis
- Publication
Russian Journal of Organic Chemistry, 2005, Vol 41, Issue 1, p144
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1007/s11178-005-0138-6