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DOI: 10.1055/a-2759-6687
Dearomative Double Diels–Alder Reaction of C-3-Substituted Indenes and Arynes
Authors
TB thanks the CSIR for the CSIR-SRF fellowship (File No. 09/081(1387)/2019-EMR-I). VG thanks ANRF for the Core Research Grant (CRG/2022/003322).
Supported by: Anusandhan National Research Foundation (ANRF) CRG/2022/003322
Dedication
Dedicated to Prof. S. Chandrasekaran on the occasion of his 80th birthday.
Abstract
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 product selectivity. A few synthetic transformations of the product have been demonstrated.
Publication History
Received: 05 October 2025
Accepted after revision: 29 November 2025
Accepted Manuscript online:
29 November 2025
Article published online:
24 December 2025
© 2025. Thieme. All rights reserved.
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