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Synthesis of a new cylindrical calix[4]arene-calix[4]pyrrole pseudo dimer

Synthesis of a new cylindrical calix[4]arene-calix[4]pyrrole pseudo dimer
Synthesis of a new cylindrical calix[4]arene-calix[4]pyrrole pseudo dimer
The synthesis of a new calixarene-capped calixpyrrole 2 has been achieved using p-tert-butylcalix[4]arene tetramethyl ketone 1 as a template. Using this approach, the stereochemistry at the calixpyrrole meso-carbons is automatically defined. The X-ray crystal structure of 2 has been elucidated and reveals hydrogen bonding between the pyrrole NH groups and the oxygens at the lower rim of the calixarene. NMR studies confirm the importance of these interactions in solution.
0040-4039
7881-7884
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Sessler, Jonathan L.
d793ea76-a3a2-4ce1-a8d5-aca7d3307fbe
Lynch, Vincent
f3e8eebc-c5fd-4c4d-9cb3-a44e24ca204d
Sansom, Petra I.
54d7fe68-651d-4dbc-b2b7-74903d77401c
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Sessler, Jonathan L.
d793ea76-a3a2-4ce1-a8d5-aca7d3307fbe
Lynch, Vincent
f3e8eebc-c5fd-4c4d-9cb3-a44e24ca204d
Sansom, Petra I.
54d7fe68-651d-4dbc-b2b7-74903d77401c

Gale, Philip A., Sessler, Jonathan L., Lynch, Vincent and Sansom, Petra I. (1996) Synthesis of a new cylindrical calix[4]arene-calix[4]pyrrole pseudo dimer. Tetrahedron Letters, 37 (44), 7881-7884. (doi:10.1016/0040-4039(96)01805-9).

Record type: Article

Abstract

The synthesis of a new calixarene-capped calixpyrrole 2 has been achieved using p-tert-butylcalix[4]arene tetramethyl ketone 1 as a template. Using this approach, the stereochemistry at the calixpyrrole meso-carbons is automatically defined. The X-ray crystal structure of 2 has been elucidated and reveals hydrogen bonding between the pyrrole NH groups and the oxygens at the lower rim of the calixarene. NMR studies confirm the importance of these interactions in solution.

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More information

Published date: 28 October 1996
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow

Identifiers

Local EPrints ID: 337255
URI: https://eprints.soton.ac.uk/id/eprint/337255
ISSN: 0040-4039
PURE UUID: 1db6cb3f-fdc4-49d6-b0f4-0ac104027094
ORCID for Philip A. Gale: ORCID iD orcid.org/0000-0001-9751-4910

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Date deposited: 20 Apr 2012 13:20
Last modified: 06 Jun 2018 12:52

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