{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T16:03:37Z","timestamp":1791302617534,"version":"4.1.0"},"reference-count":55,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2007,11,8]],"date-time":"2007-11-08T00:00:00Z","timestamp":1194480000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2008,1,18]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Environmentally friendly oxidation of primary aliphatic amines to imines has been successfully achieved, under metal\u2010free conditions, by the use of diverse electrogenerated\n                    <jats:italic>o<\/jats:italic>\n                    \u2010azaquinone mediators. High catalytic performance, together with high chemoselectivity, were observed with electron\u2010poor\n                    <jats:italic>o<\/jats:italic>\n                    \u2010azaquinone catalysts generated from 2\u2010aminoresorcinol derivatives. Similar to copper amine oxidase enzymes, these mediators exhibited lower reactivity toward \u03b1\u2010branched primary amines and no reactivity toward secondary amines. In the case of 3,4\u2010aminophenol derivatives lacking a 2\u2010hydroxy group, the generated\n                    <jats:italic>o<\/jats:italic>\n                    \u2010azaquinone species failed to catalyze the oxidation of the amine to the corresponding imine. Further mechanistic considerations allowed a rationalization of the crucial role of the 2\u2010hydroxy group in converting a catalytically inert species into a highly effective biomimetic catalyst.\n                  <\/jats:p>","DOI":"10.1002\/chem.200700876","type":"journal-article","created":{"date-parts":[[2007,11,8]],"date-time":"2007-11-08T11:53:13Z","timestamp":1194522793000},"page":"996-1003","source":"Crossref","is-referenced-by-count":111,"title":["Environmentally Friendly Chemoselective Oxidation of Primary Aliphatic Amines by Using a Biomimetic Electrocatalytic System"],"prefix":"10.1002","volume":"14","author":[{"given":"Martine","family":"Largeron","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ang\u00e8le","family":"Chiaroni","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maurice\u2010Bernard","family":"Fleury","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2008,1,10]]},"reference":[{"key":"e_1_2_5_1_2","doi-asserted-by":"publisher","DOI":"10.1039\/a808142e"},{"key":"e_1_2_5_2_2","unstructured":"\u00a0"},{"key":"e_1_2_5_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200390596"},{"key":"e_1_2_5_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200352076"},{"key":"e_1_2_5_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0400382"},{"key":"e_1_2_5_5_2","unstructured":"For selected recent examples see:"},{"key":"e_1_2_5_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/b202117j"},{"key":"e_1_2_5_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200250779"},{"key":"e_1_2_5_7_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200250779"},{"key":"e_1_2_5_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200401082"},{"key":"e_1_2_5_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2006.09.088"},{"key":"e_1_2_5_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/b615805f"},{"key":"e_1_2_5_11_2","unstructured":"For recent examples see:"},{"key":"e_1_2_5_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/b009944i"},{"key":"e_1_2_5_13_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.76.2399"},{"key":"e_1_2_5_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200304916"},{"key":"e_1_2_5_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jcat.2004.11.034"},{"key":"e_1_2_5_16_2","unstructured":"\u00a0"},{"key":"e_1_2_5_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo035336g"},{"key":"e_1_2_5_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2004.07.063"},{"key":"e_1_2_5_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2005.04.035"},{"key":"e_1_2_5_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2005.05.069"},{"key":"e_1_2_5_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar9703342"},{"key":"e_1_2_5_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi020246b"},{"key":"e_1_2_5_23_2","unstructured":"\u00a0"},{"key":"e_1_2_5_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00139a003"},{"key":"e_1_2_5_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00153a001"},{"key":"e_1_2_5_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo961705f"},{"key":"e_1_2_5_27_2","doi-asserted-by":"publisher","DOI":"10.1006\/bioo.1998.1130"},{"key":"e_1_2_5_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja011141j"},{"key":"e_1_2_5_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0020207"},{"key":"e_1_2_5_30_2","unstructured":"\u00a0"},{"key":"e_1_2_5_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo000478l"},{"key":"e_1_2_5_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200390238"},{"key":"e_1_2_5_32_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200390263"},{"key":"e_1_2_5_33_2","doi-asserted-by":"publisher","DOI":"10.1039\/a608275k"},{"key":"e_1_2_5_34_2","unstructured":"\u00a0"},{"key":"e_1_2_5_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00069a008"},{"key":"e_1_2_5_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00024a030"},{"key":"e_1_2_5_37_2","unstructured":"It may be noted that in the three analyzed compounds all the hydrogen atoms belonging to the nitrogen atom N3 and to the different hydroxy groups are engaged in either inter\u2010 or intramolecular hydrogen bonds. As shown in Figure\u20051 a strong intramolecular hydrogen bond is established between the hydroxy group O2\u2010H and the carbonyl oxygen atom O7 with the following characteristics: for7red distances O2\u22c5\u22c5\u22c5O7=2.524(2)\u2005\u00c5 O2\u2013H=0.92\u2005\u00c5 H\u22c5\u22c5\u22c5O7=1.68\u2005\u00c5 angle O2\u22c5\u22c5\u22c5H\u22c5\u22c5\u22c5O7=151.4\u00b0; for9red distances O2\u22c5\u22c5\u22c5O7=2.573(2)\u2005\u00c5 O2\u2013H=0.84\u2005\u00c5 H\u22c5\u22c5\u22c5O7=1.81\u2005\u00c5 angle O2\u22c5\u22c5\u22c5H\u22c5\u22c5\u22c5O7=151.5\u00b0; for11red distances O2\u22c5\u22c5\u22c5O7=2.562(2)\u2005\u00c5 O2\u2013H=0.82\u2005\u00c5 H\u22c5\u22c5\u22c5O7=1.80\u2005\u00c5 angle O2\u22c5\u22c5\u22c5H\u22c5\u22c5\u22c5O7=153.4\u00b0 and in this last compound there is a second hydrogen bond between the hydroxy group O2\u2032\u2013H and the oxygen atom O7 with the respective geometry as follows: distances O2\u2032\u22c5\u22c5\u22c5O7=2.584(2)\u2005\u00c5 O2\u2032\u2013H=0.93\u2005\u00c5 H\u22c5\u22c5\u22c5O7=1.76\u2005\u00c5 angle O2\u2032\u22c5\u22c5\u22c5H\u22c5\u22c5\u22c5O7=145.9\u00b0 aligning the three oxygen atoms (angle O2\u22c5\u22c5\u22c5O7\u22c5\u22c5\u22c5O2\u2032=178.2\u00b0). In the three compounds7red 9red and11red the two phenyl rings are tilted by 43.9 72.6 and 42.3\u00b0 respectively."},{"key":"e_1_2_5_38_2","unstructured":"\u00a0"},{"key":"e_1_2_5_39_2","first-page":"2597","author":"Miyabe H.","year":"2004","journal-title":"Synlett"},{"key":"e_1_2_5_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo052518x"},{"key":"e_1_2_5_41_2","unstructured":"\u00a0"},{"key":"e_1_2_5_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20020301)114:5<852::AID-ANGE852>3.0.CO;2-B"},{"key":"e_1_2_5_42_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020301)41:5<824::AID-ANIE824>3.0.CO;2-Z"},{"key":"e_1_2_5_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo035614b"},{"key":"e_1_2_5_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm040874m"},{"key":"e_1_2_5_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo060452f"},{"key":"e_1_2_5_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(99)00504-1"},{"key":"e_1_2_5_47_2","unstructured":"\u00a0"},{"key":"e_1_2_5_48_2","first-page":"1870","volume":"56","author":"Lindner H.","year":"1923","journal-title":"Chem. Ber."},{"key":"e_1_2_5_49_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2004.02.063"},{"key":"e_1_2_5_50_2","first-page":"931","author":"Tseiltlin G. M.","year":"1982","journal-title":"J. Org. Chem. USSR (Engl. Transl.)"},{"key":"e_1_2_5_51_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1989-27361"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.200700876","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.200700876","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T22:09:47Z","timestamp":1760306987000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.200700876"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2008,1,10]]},"references-count":55,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2008,1,18]]}},"alternative-id":["10.1002\/chem.200700876"],"URL":"https:\/\/doi.org\/10.1002\/chem.200700876","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2008,1,10]]}}}