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Synfacts 2025; 21(07): 683
DOI: 10.1055/a-2601-4089
DOI: 10.1055/a-2601-4089
Synthesis of Materials and Unnatural Products
From Cycloheptatriene to Conjugated Z,Z,Z-Trienes
Ton NHH,
Mai BK,
Fallon T,
Nguyen TV *.
University of New South Wales, Sydney, Australia
Rapid Access to Conjugated Z,Z,Z-Trienes.
Angew. Chem. Int. Ed. 2025;
64: e202502713
DOI: 10.1002/anie.202502713
Rapid Access to Conjugated Z,Z,Z-Trienes.
Angew. Chem. Int. Ed. 2025;
64: e202502713
DOI: 10.1002/anie.202502713
Significance
An efficient synthesis of conjugated Z,Z,Z-trienes from cycloheptatriene is reported, featuring a nucleophile-intercepted Beckman fragmentation reaction.
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Comment
Taking the readily available tropone oxime tosylate as the substrate, the reaction is suggested to have a bicyclic azirine intermediate according to the calculations.
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Publication History
Article published online:
23 June 2025
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