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We acknowledge the European Research Council (ERC) under the European Union’s Horizon 2020 research and innovation program (ERC-2015-STG-677023 and ERC-2013-SYG-610256 NANOCOSMOS) and the innovation program under grant agreement No. 696656 (GrapheneCore1-Graphene-based disruptive technologies) and grant agreement No. 785219 (GrapheneCore2-Graphene-based disruptive technologies) for financial support. Grants PGC2018-101181-B-I00 and MAT2017-85089-C2-1-R funded by MCIN/AEI/ 10.13039/501100011033 and “ERDF A way of making Europe” by the “European Union”, and grant PID2020-113142RB-C21 funded by MCIN/AEI/ 10.13039/501100 011033 also provided financial support. We also acknowledge Comunidad de Madrid via Programa de Investigación Tecnologías 2018 (FOTOART-CM S2018/NMT-4367), the Swiss National Science Foundation (grant number 200020-182015), the NCCR MARVEL funded by the Swiss National Science Foundation (grant number 51NF40-182892) and FEDER/Junta de Andalucía-Consejería de Economía y Conocimiento (B-FQM-428-UGR20). C. S. S. and N. R. A. acknowledge Grants RYC2018-024364-I and BES-2015-072642, respectively, funded by MCIN/AEI/ 10.13039/501100011033 and “ESF Investing in your future”. I. R. M. acknowledges the University of Granada for her postdoctoral contract (Contrato Puente-Plan Propio UGR). F.V. thanks Ministerio de Universidades for the FPU grant (FPU18/05938)., On-surface synthesis, complementary to wet chemistry, has been demonstrated to be a valid approach for the synthesis of tailored graphenic nanostructures with atomic precision. Among the different existing strategies used to tune the optoelectronic and magnetic properties of these nanostructures, the introduction of non-hexagonal rings inducing out-of-plane distortions is a promising pathway that has been scarcely explored on surfaces. Here, we demonstrate that non-hexagonal rings, in the form of tropone (cycloheptatrienone) moieties, are thermally transformed into phenyl or cyclopentadienone moieties upon an unprecedented surface-mediated retro–Buchner-type reaction involving a decarbonylation or an intramolecular rearrangement of the CO unit, respectively., Junta de Andalucía-Consejería de Economía y Conocimiento B-FQM-428-UGR20, BES-2015-072642, RYC2018-024364-I, MCIN, Ministerio de Universidades FPU18/05938, European Commission FOTOART-CM S2018/NMT-4367, European Research Council, Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung 200020-182015, European Social Fund, Universidad de Granada, European Regional Development Fund 011033, PID2020-113142RB-C21, S2018/NMT-4367, National Center of Competence in Research Materials’ Revolution: Computational Design and Discovery of Novel Materials 51NF40-182892, Agencia Estatal de Investigación