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While thermoreversible furan-maleimide Diels–Alder adducts are often employed as dynamic bonds in CANs, the tendency of these systems to undergo irreversible side reactions prompted our exploration of new dynamic pairings. Higher order [6+4] additions of tropones and dienes have been investigated since the 1960s, however, little work has been done to examine the factors that influence their potentially dynamic behavior. Herein, we report a synergistic computational and experimental method toward the design of reversible cycloadditions with substituted tropones and cyclic dienes. Using the cycloadditions of 2-cyanotropone and cyclopentadiene to experimentally validate computational groundwork set by DFT calculations at the m062x-6-31G(d) level of theory, we find a reasonable agreement between predicted activation barriers and the experimental distribution of [6+4] and competitive [4+2] cycloadducts. At elevated temperatures, we observed the rapid cycloreversion of the [6+4] adduct, forming the more stable [4+2] adduct which remarkably exhibited some dissociation. The alignment of our initial theoretical and experimental screening reinforces the potential of this dual approach for crafting novel reversible cycloadducts.</p>"},{"label":"Digital Identifier","value":"b2026-ixcoyperez"},{"label":"Digital Object Identifier (DOI)","value":"https://doi.org/10.14418/0ktnywa0"},{"label":"Digital Origin","value":["born digital"]},{"label":"Discipline","value":["Chemistry"]},{"label":"Date","value":"April 15, 2026"},{"label":"EDTF Date","value":"D:00 M:00 Y:2026"},{"label":"File Format","value":["application/pdf"]},{"label":"Genre","value":["theses"]},{"label":"Group","value":["Theses & Dissertations"]},{"label":"Held By","value":"Wesleyan University Library, Wesleyan University, Middletown, CT, USA"},{"label":"Language","value":["English"]},{"label":"Repository","value":["University Archives"]},{"label":"Rights","value":["In Copyright"]},{"label":"Thesis Advisor(s)","value":["Elling, Ben"]},{"label":"Type","value":["Text"]}],"description":"Selective and 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