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Their degradation initiated by the gas-phase reaction with hydroxyl radicals (OH) forms mainly bicyclic peroxy radicals (BCP) besides phenol-type compounds. The formation of highly oxidized products with at least 6\u2009O atoms (HOMs) starting from BCP is currently controversial. Here, the experimental observation of HOMs and other products is reported for near-atmospheric conditions focusing on OH + toluene. Autoxidation processes starting from BCP generate C\n 7<\/jats:sub>\n H\n 9<\/jats:sub>\n O\n 7<\/jats:sub>\n and C\n 7<\/jats:sub>\n H\n 9<\/jats:sub>\n O\n 9<\/jats:sub>\n radicals with molar yields of\n \n \n $${0.25}_{\\,-0.13}^{\\,+0.25}\\, \\%$$<\/jats:tex-math>\n \n \n \n 0.25<\/mml:mn>\n <\/mml:mrow>\n \n \n \u2212<\/mml:mo>\n 0.13<\/mml:mn>\n <\/mml:mrow>\n \n \n +<\/mml:mo>\n 0.25<\/mml:mn>\n <\/mml:mrow>\n <\/mml:msubsup>\n \n %<\/mml:mi>\n <\/mml:math>\n <\/jats:alternatives>\n <\/jats:inline-formula>\n and\n \n \n $${0.12}_{\\,-0.06}^{\\,+0.12}\\, \\%$$<\/jats:tex-math>\n \n \n \n 0.12<\/mml:mn>\n <\/mml:mrow>\n \n \n \u2212<\/mml:mo>\n 0.06<\/mml:mn>\n <\/mml:mrow>\n \n \n +<\/mml:mo>\n 0.12<\/mml:mn>\n <\/mml:mrow>\n <\/mml:msubsup>\n \n %<\/mml:mi>\n <\/mml:math>\n <\/jats:alternatives>\n <\/jats:inline-formula>\n , respectively. Labeling experiments revealed that the ring H atoms are involved in autoxidation. The atmospherically relevant reaction of C\n 7<\/jats:sub>\n H\n 9<\/jats:sub>\n O\n 7<\/jats:sub>\n and C\n 7<\/jats:sub>\n H\n 9<\/jats:sub>\n O\n 9<\/jats:sub>\n with NO almost exclusively forms organic nitrates as HOM products, C\n 7<\/jats:sub>\n H\n 9<\/jats:sub>\n O\n 6-8<\/jats:sub>\n NO\n 2<\/jats:sub>\n , with a total molar yield \u2264 0.1%. Other HOMs, such as C\n 7<\/jats:sub>\n H\n 8<\/jats:sub>\n O\n 8<\/jats:sub>\n and C\n 7<\/jats:sub>\n H\n 8<\/jats:sub>\n O\n 10<\/jats:sub>\n , represent only small trace products. Results from OH + benzene confirmed the findings from the toluene system pointing to a minor relevance of both aromatics for HOM generation.\n <\/jats:p>","DOI":"10.1038\/s42004-026-02230-0","type":"journal-article","created":{"date-parts":[[2026,10,8]],"date-time":"2026-10-08T13:06:10Z","timestamp":1791464770000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Highly oxidized products from the atmospheric reaction of hydroxyl radicals with toluene"],"prefix":"10.1038","volume":"9","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2014-6018","authenticated-orcid":false,"given":"Torsten","family":"Berndt","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2026,10,8]]},"reference":[{"key":"2230_CR1","doi-asserted-by":"publisher","first-page":"6931","DOI":"10.5194\/acp-16-6931-2016","volume":"16","author":"D Cabrera-Perez","year":"2016","unstructured":"Cabrera-Perez, D., Taraborrelli, D., Sander, R. & Pozzer, A. Global atmospheric budget of simple monocyclic aromatic compounds. Atmos. Chem. Phys. 16, 6931\u20136947 https:\/\/doi.org\/10.5194\/acp-16-6931-2016 (2016).","journal-title":"Atmos. Chem. Phys."},{"key":"2230_CR2","doi-asserted-by":"publisher","first-page":"7017","DOI":"10.5194\/acp-10-7017-2010","volume":"10","author":"JF Lamarque","year":"2010","unstructured":"Lamarque, J. F. et al. Historical (1850-2000) gridded anthropogenic and biomass burning emissions of reactive gases and aerosols: methodology and application. Atmos. Chem. Phys. 10, 7017\u20137039 https:\/\/doi.org\/10.5194\/acp-10-7017-2010 (2010).","journal-title":"Atmos. Chem. Phys."},{"key":"2230_CR3","doi-asserted-by":"publisher","first-page":"22279","DOI":"10.1039\/d0cp02984j","volume":"22","author":"X Wu","year":"2020","unstructured":"Wu, X., Huang, C., Niu, S. & Zhang, F. New theoretical insights into the reaction kinetics of toluene and hydroxyl radicals. Phys. Chem. Chem. 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