Bicyclo[1.1.1]pentane Embedded in Porphyrinoids.
Bicyclo[1.1.1]Pentane
Calix[4]Pyrrole
Grignard Reagents
Macrocycles
Porphyrinoids
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
26 Jun 2023
26 Jun 2023
Historique:
received:
23
02
2023
medline:
30
3
2023
pubmed:
30
3
2023
entrez:
29
3
2023
Statut:
ppublish
Résumé
We report a two-step approach to obtain synthetically versatile bicyclo[1.1.1]pentane (BCP) derivatives using Grignard reagents. This method allows the incorporation of BCP units in tetrapyrrolic macrocycles and the synthesis of a new class of calix[4]pyrrole analogues by replacing two bridging methylene groups with two BCP units. In addition, a doubly N-confused system was also formed in the presence of electron-withdrawing substituents at the BCP bridgeheads. The pyrrole rings in BCP containing macrocycles exist in 1,3-alternate or αβαβ conformations, as observed from single-crystal X-ray diffraction analyses and 2D NMR spectroscopy.
Identifiants
pubmed: 36988343
doi: 10.1002/anie.202302771
doi:
Substances chimiques
pentane
4FEX897A91
Pentanes
0
Pyrroles
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202302771Subventions
Organisme : Science Foundation Ireland
ID : 21/FFP-A/9469
Pays : Ireland
Informations de copyright
© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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