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We envisioned that the assembly of tyrosine\/tyrosyl radical couples with interfacial water molecules would realize a biomimetic stacking hydrogen atom transfer (HAT) transition state to facilitate the electron\u2010transfer process. The optimal organic nitrite, 2\u2010methoxyethyl nitrite, resulted in rapid coupling of the tyrosyl radicals with \u22c5NO<jats:sub>2<\/jats:sub> at the oil\u2013water interface to afford the nitrated phenols. Many characteristics found in our on\u2010water strategy are distinct from other complementary systems that include radical nitration. These enticing roles of water in the reaction process introduce new avenues to explore in the design of synthetic organic chemistry systems.<\/jats:p>","DOI":"10.1002\/asia.202200457","type":"journal-article","created":{"date-parts":[[2022,5,25]],"date-time":"2022-05-25T10:51:35Z","timestamp":1653475895000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["2\u2010Methoxyethyl Nitrite as a Reagent for Chemoselective On\u2010Water Nitration"],"prefix":"10.1002","volume":"17","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0743-1420","authenticated-orcid":false,"given":"Taku","family":"Kitanosono","sequence":"first","affiliation":[{"name":"Department of Chemistry School of Science The University of Tokyo  Hongo, Bunkyo-ku Tokyo 113-0033 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Airu","family":"Hashidoko","sequence":"additional","affiliation":[{"name":"Department of Chemistry School of Science The University of Tokyo  Hongo, Bunkyo-ku Tokyo 113-0033 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yasuhiro","family":"Yamashita","sequence":"additional","affiliation":[{"name":"Department of Chemistry School of Science The University of Tokyo  Hongo, Bunkyo-ku Tokyo 113-0033 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8235-4368","authenticated-orcid":false,"given":"Sh\u016b","family":"Kobayashi","sequence":"additional","affiliation":[{"name":"Department of Chemistry School of Science The University of Tokyo  Hongo, Bunkyo-ku Tokyo 113-0033 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2022,6,15]]},"reference":[{"key":"e_1_2_8_1_1","unstructured":"Authoritative reviews see:"},{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.1c00045"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201905482"},{"key":"e_1_2_8_4_2","first-page":"99","volume-title":"Biphasic Chemistry and the Solvent Case","author":"Scherrmann M.-C."},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/slct.201903360"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100162c"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41570-020-0203-2"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462883"},{"key":"e_1_2_8_9_1","unstructured":"\u00a0"},{"key":"e_1_2_8_10_2","doi-asserted-by":"publisher","DOI":"10.1080\/00268976.2020.1797920"},{"key":"e_1_2_8_11_2","first-page":"5492","volume":"129","author":"Jung Y.","year":"2007","journal-title":"Chem. 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