Selective functionalization of cavitands: synthesis of a new hemicarcerand


Timmerman, Peter and Mook, Maarten G.A. van and Verboom, Willem and Hummel, Gerrit J. van and Harkema, Sybolt and Reinhoudt, David N. (1992) Selective functionalization of cavitands: synthesis of a new hemicarcerand. Tetrahedron Letters, 33 (23). pp. 3377-3380. ISSN 0040-4039

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Abstract: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.
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Copyright:© 1992 Elsevier Science
Science and Technology (TNW)
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Metis ID: 106735