Toward a Formyl-to-Phenyl Conversion: An Unexpected Photochemical Fulvene Rearrangement.
Cyclopropanes
Fulvenes
Photochemistry
Rearrangement
Spiro-Compounds
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:
28 Aug 2023
28 Aug 2023
Historique:
received:
02
03
2023
medline:
17
6
2023
pubmed:
17
6
2023
entrez:
17
6
2023
Statut:
ppublish
Résumé
Toward a conversion of aldehydes into arenes, we designed a sequence involving the initial reaction of an aldehyde to give a fulvene, followed by photochemical and platinum-catalyzed rearrangements into a Dewar benzene derivative, which finally isomerizes into the targeted arene. While computational studies support the plausibility of this route, we found that fulvene irradiation resulted in an unexpected isomerization into a spiro[2.4]heptadiene. This unusual photorearrangement has been investigated mechanistically and provides access to a variety of spiro[2.4]heptadienes with different substituents.
Identifiants
pubmed: 37329283
doi: 10.1002/anie.202303119
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202303119Subventions
Organisme : Deutsche Forschungsgemeinschaft
Organisme : Verband der Chemischen Industrie
Informations de copyright
© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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