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Microwave‐Assisted [4+2] Diels–Alder Cycloaddition of 1,4‐Diethynyl Triptycene with Various Cyclopentadienone Derivatives: Promising Building Blocks for Polymer Networks
Author(s) -
Alameddine Bassam,
Baig Noorullah,
Shetty Suchetha,
AlSagheer Fakhreia,
AlMousawi Saleh
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700655
Subject(s) - triptycene , chemistry , cycloaddition , tetra , palladium , diels–alder reaction , catalysis , nuclear magnetic resonance spectroscopy , polymer chemistry , combinatorial chemistry , organic chemistry , photochemistry , medicinal chemistry
Abstract Triptycene derivatives substituted at their 1,4‐ positions with tetraphenylbenzene and diphenyltriphenylene moieties were prepared by microwave‐assisted [4+2] Diels–Alder cycloaddition reactions in very good yields. The target compounds were characterized by 1 H and 13 C NMR spectroscopy, HRMS, UV/Vis and emission spectrophotometry. In addition, single crystal XRD spectra for two of these derivatives are presented. The tetra‐ and octabrominated triptycene compounds underwent palladium‐catalyzed Suzuki–Miyaura cross‐coupling reactions affording the desired products in very good yields. This successful tetra‐ and octa‐fold substitution paves the way for the employment of these building blocks to prepare polymer networks for various applications.