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Synlett
DOI: 10.1055/a-2759-6687
Letter

Dearomative Double Diels-Alder Reaction of C-3 Substituted Indenes and Arynes

Autoren

  • Tamal Ballav

    1   Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur, India (Ringgold ID: RIN30133)

  • Venkataraman Ganesh 

    1   Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur, India (Ringgold ID: RIN30133)

Gefördert durch: Ministry of Education, Council for Scientific and Industrial Research 09/ 081(1387)/2019-EMR-I
Gefördert durch: Anusandhan National Research Foundation (ANRF) CRG/2022/003322
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We report the dearomative [4+2]/[4+2] (double Diels-Alder) reaction of C-3 substituted indenes and benzyne to afford a new class of bridged polycyclic hydrocarbon derivatives of the methanotetraphene family. Without C-3 substitution, the reaction proceeded via a [4+2]/[2+2] cycloaddition reaction. DFT studies compared the decisive effect of the C-3 substituent on the importance of the substitution on the product selectivity. A few synthetic transformations of the product have been demonstrated.



Publikationsverlauf

Eingereicht: 05. Oktober 2025

Angenommen nach Revision: 29. November 2025

Accepted Manuscript online:
29. November 2025

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