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Lithiation of meso-octamethylcalix[4]pyrrole: a general route to C-rim monosubstituted calix[4]pyrroles

Lithiation of meso-octamethylcalix[4]pyrrole: a general route to C-rim monosubstituted calix[4]pyrroles
Lithiation of meso-octamethylcalix[4]pyrrole: a general route to C-rim monosubstituted calix[4]pyrroles
Lithiation and subsequent addition of an electrophile to meso-octamethylcalix[4]pyrrole provides a straightforward synthetic route to new, C-rim monosubstituted calix[4]pyrroles. A variety of electrophiles were used, resulting in calix[4]pyrroles with appended functional groups including carboxyl, ester, iodo, and formyl. This method was optimized to give maximum yields of the monosubstituted derivatives with lowest possible contamination by di- and trisubstituted congeners. Solid-state studies, performed for a number of these derivatives, showed unexpected supramolecular interactions involving both solvents and the monosubstituted calix[4]pyrrole derivatives themselves.
calixpyrrole, anion binding, synthesis, porphyrinogen
0022-3263
7641-7645
Anzenbacher Jr, Pavel
b14c77d4-d505-4e16-8f05-aa4df7647be5
Jursíková, Karolina
057682b3-1a88-405d-90f9-da2a58696bdc
Shriver, James A.
9d032547-881d-48bc-b9b1-1814921b423a
Miyaji, Hidekazu
2c6e1e61-3ad7-46e6-86de-2f46dfb57333
Lynch, Vincent M.
1ca6d39d-b02d-4141-ab55-f566f00a09b5
Sessler, Jonathan L.
d793ea76-a3a2-4ce1-a8d5-aca7d3307fbe
Gale, Philip A.
ce0aa62f-d081-408b-8b00-6d954058afab
Anzenbacher Jr, Pavel
b14c77d4-d505-4e16-8f05-aa4df7647be5
Jursíková, Karolina
057682b3-1a88-405d-90f9-da2a58696bdc
Shriver, James A.
9d032547-881d-48bc-b9b1-1814921b423a
Miyaji, Hidekazu
2c6e1e61-3ad7-46e6-86de-2f46dfb57333
Lynch, Vincent M.
1ca6d39d-b02d-4141-ab55-f566f00a09b5
Sessler, Jonathan L.
d793ea76-a3a2-4ce1-a8d5-aca7d3307fbe
Gale, Philip A.
ce0aa62f-d081-408b-8b00-6d954058afab

Anzenbacher Jr, Pavel, Jursíková, Karolina, Shriver, James A., Miyaji, Hidekazu, Lynch, Vincent M., Sessler, Jonathan L. and Gale, Philip A. (2000) Lithiation of meso-octamethylcalix[4]pyrrole: a general route to C-rim monosubstituted calix[4]pyrroles. Journal of Organic Chemistry, 65, 7641-7645. (doi:10.1021/jo005610w).

Record type: Article

Abstract

Lithiation and subsequent addition of an electrophile to meso-octamethylcalix[4]pyrrole provides a straightforward synthetic route to new, C-rim monosubstituted calix[4]pyrroles. A variety of electrophiles were used, resulting in calix[4]pyrroles with appended functional groups including carboxyl, ester, iodo, and formyl. This method was optimized to give maximum yields of the monosubstituted derivatives with lowest possible contamination by di- and trisubstituted congeners. Solid-state studies, performed for a number of these derivatives, showed unexpected supramolecular interactions involving both solvents and the monosubstituted calix[4]pyrrole derivatives themselves.

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Published date: 2000
Keywords: calixpyrrole, anion binding, synthesis, porphyrinogen

Identifiers

Local EPrints ID: 13603
URI: http://eprints.soton.ac.uk/id/eprint/13603
ISSN: 0022-3263
PURE UUID: 04307c9b-b859-4775-b55c-f0de6824764b

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Date deposited: 16 Dec 2004
Last modified: 15 Jul 2019 19:35

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Contributors

Author: Pavel Anzenbacher Jr
Author: Karolina Jursíková
Author: James A. Shriver
Author: Hidekazu Miyaji
Author: Vincent M. Lynch
Author: Jonathan L. Sessler
Author: Philip A. Gale

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