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

doi:10.1016/S0040-4039(00)92093-8

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

Research output: Contribution to journal › Article › Academic › peer-review

33 Citations (Scopus)

722 Downloads (Pure)

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 language	Undefined
Pages (from-to)	3377-3380
Number of pages	4
Journal	Tetrahedron letters
Volume	0
Issue number	33
DOIs	https://doi.org/10.1016/S0040-4039(00)92093-8
Publication status	Published - 1992

Keywords

METIS-106735
IR-12554

Access to Document

10.1016/S0040-4039(00)92093-8

K12554__

Cite this

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title = "Selective functionalization of cavitands: synthesis of a new hemicarcerand",

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.",

keywords = "METIS-106735, IR-12554",

author = "P. Timmerman and \{van Mook\}, \{Maarten G.A.\} and Willem Verboom and \{van Hummel\}, G.J. and Sybolt Harkema and David Reinhoudt",

year = "1992",

doi = "10.1016/S0040-4039(00)92093-8",

language = "Undefined",

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pages = "3377--3380",

journal = "Tetrahedron letters",

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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

SN - 0040-4039

VL - 0

SP - 3377

EP - 3380

JO - Tetrahedron letters

JF - Tetrahedron letters

IS - 33

ER -