Selective functionalization of cavitands: synthesis of a new hemicarcerand

P. Timmerman, Maarten G.A. van Mook, Willem Verboom, G.J. van Hummel, Sybolt Harkema, David Reinhoudt

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Partly bridged cavitands 2 and 4 can be selectively debrominated in one step by treatment with 5 equiv of n-BuLi in THF to afford the corresponding dibromo derivatives 5 and 6 in 90% and 77% yield, respectively. After incorporatin of the fourth bridge, the remaining two bromines can be replaced by CN to give 9 (95%), (C(O)OMe to give 10 (60%) or OH to give 11 (62%). Two molecules of 11 were coupled with CH2BrCl in DMSO/THF under high dilution conditions to give new hemicarcerand 12 in 71% yield.
Original languageUndefined
Pages (from-to)3377-3380
Number of pages4
JournalTetrahedron letters
Issue number33
Publication statusPublished - 1992


  • METIS-106735
  • IR-12554

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