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Toward a Formyl‐to‐Phenyl Conversion: An Unexpected Photochemical Fulvene Rearrangement.

Toward a Formyl‐to‐Phenyl Conversion: An Unexpected Photochemical Fulvene Rearrangement.

Authors :
Lindner, Monika M.
Alachraf, M. Wasim
Mitschke, Benjamin
Schulze, Philipp
Leutzsch, Markus
List, Benjamin
Source :
Angewandte Chemie International Edition. 8/28/2023, Vol. 62 Issue 35, p1-6. 6p.
Publication Year :
2023

Abstract

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. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
14337851
Volume :
62
Issue :
35
Database :
Academic Search Index
Journal :
Angewandte Chemie International Edition
Publication Type :
Academic Journal
Accession number :
170078919
Full Text :
https://doi.org/10.1002/anie.202303119