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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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.
Original languageUndefined
Pages (from-to)3377-3380
Number of pages4
JournalTetrahedron letters
Volume0
Issue number33
DOIs
Publication statusPublished - 1992

Keywords

  • METIS-106735
  • IR-12554

Cite this

Timmerman, P. ; van Mook, Maarten G.A. ; Verboom, Willem ; van Hummel, G.J. ; Harkema, Sybolt ; Reinhoudt, David. / Selective functionalization of cavitands: synthesis of a new hemicarcerand. In: Tetrahedron letters. 1992 ; Vol. 0, No. 33. pp. 3377-3380.
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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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Selective functionalization of cavitands: synthesis of a new hemicarcerand. / Timmerman, P.; van Mook, Maarten G.A.; Verboom, Willem; van Hummel, G.J.; Harkema, Sybolt; Reinhoudt, David.

In: Tetrahedron letters, Vol. 0, No. 33, 1992, p. 3377-3380.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Selective functionalization of cavitands: synthesis of a new hemicarcerand

AU - Timmerman, P.

AU - van Mook, Maarten G.A.

AU - Verboom, Willem

AU - van Hummel, G.J.

AU - Harkema, Sybolt

AU - Reinhoudt, David

PY - 1992

Y1 - 1992

N2 - 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.

AB - 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.

KW - METIS-106735

KW - IR-12554

U2 - 10.1016/S0040-4039(00)92093-8

DO - 10.1016/S0040-4039(00)92093-8

M3 - Article

VL - 0

SP - 3377

EP - 3380

JO - Tetrahedron letters

JF - Tetrahedron letters

SN - 0040-4039

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ER -