{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,14]],"date-time":"2025-10-14T01:07:30Z","timestamp":1760404050558,"version":"build-2065373602"},"reference-count":52,"publisher":"Wiley","issue":"22","license":[{"start":{"date-parts":[[2005,9,27]],"date-time":"2005-09-27T00:00:00Z","timestamp":1127779200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Eur J Org Chem"],"published-print":{"date-parts":[[2005,11]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Reductive intramolecular cyclization of ethyl 2\u2010bromo\u20103\u2010(3\u2032,4\u2032\u2010methylenedioxyphenyl)\u20103\u2010(propargyloxy)propanoate(<jats:bold>1<\/jats:bold>) and ethyl 3\u2010allyloxy\u20102\u2010bromo\u20103\u2010(3\u2032,4\u2032\u2010dimethoxyphenyl)propanoate (<jats:bold>2<\/jats:bold>) promoted by (1,4,8,11\u2010tetramethyl\u20101,4,8,11\u2010tetraazacyclotetradecane)nickel(<jats:sc>I<\/jats:sc>), [Ni(tmc)]<jats:sup>+<\/jats:sup>, electrogenerated at glassy\u2010carbon cathodes in dimethylformamide containing tetraalkylammonium salts, has been investigated. Cyclic voltammograms for reduction of [Ni(tmc)]<jats:sup>2+<\/jats:sup> in the presence of <jats:bold>1<\/jats:bold> and <jats:bold>2<\/jats:bold> reveal that [Ni(tmc)]<jats:sup>+<\/jats:sup> catalytically reduces these two compounds at potentials significantly more positive than those required for direct reduction of the bromo esters. During controlled\u2010potential electrolyses of solutions of [Ni(tmc)]<jats:sup>2+<\/jats:sup> in the presence of <jats:bold>1<\/jats:bold> and <jats:bold>2<\/jats:bold>, catalytic reduction of each substrate proceeds by one\u2010electron cleavage of the carbon\u2013bromine bond to form a radical intermediate that undergoes cyclization to afford, respectively, ethyl 2\u2010(3\u2032,4\u2032\u2010methylenedioxyphenyl)\u20104\u2010methylenetetrahydrofuran\u20103\u2010carboxylate (<jats:bold>3<\/jats:bold>) and ethyl 2\u2010(3\u2032,4\u2032\u2010dimethoxyphenyl)\u20104\u2010methyltetrahydrofuran\u20103\u2010carboxylate (<jats:bold>6<\/jats:bold>). A mechanistic Scheme is proposed to account for the formation of each major product. (\u00a9 Wiley\u2010VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2005)<\/jats:p>","DOI":"10.1002\/ejoc.200500478","type":"journal-article","created":{"date-parts":[[2005,9,27]],"date-time":"2005-09-27T11:47:04Z","timestamp":1127821624000},"page":"4852-4859","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":22,"title":["Electroreductive Radical Cyclization of Ethyl 2\u2010Bromo\u20103\u2010allyloxy\u2010 and\u20103\u2010(propargyloxy)propanoates Catalyzed by (Tetramethylcyclam)nickel(<scp>I<\/scp>) Electrogenerated at Carbon Cathodes in Dimethylformamide"],"prefix":"10.1002","volume":"2005","author":[{"given":"Ana P.","family":"Esteves","sequence":"first","affiliation":[]},{"given":"Danielle M.","family":"Goken","sequence":"additional","affiliation":[]},{"given":"Lee J.","family":"Klein","sequence":"additional","affiliation":[]},{"given":"Luis F. M.","family":"Leite","sequence":"additional","affiliation":[]},{"given":"Maria J.","family":"Medeiros","sequence":"additional","affiliation":[]},{"given":"Dennis G.","family":"Peters","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2005,11,3]]},"reference":[{"volume-title":"Radicals in Organic Synthesis:","year":"1986","author":"Giese B.","key":"e_1_2_5_1_2"},{"doi-asserted-by":"publisher","key":"e_1_2_5_2_2","DOI":"10.1039\/cs9932200143"},{"doi-asserted-by":"publisher","key":"e_1_2_5_3_2","DOI":"10.1039\/p19960001015"},{"doi-asserted-by":"publisher","key":"e_1_2_5_4_2","DOI":"10.1021\/ja00349a067"},{"doi-asserted-by":"publisher","key":"e_1_2_5_5_2","DOI":"10.1016\/S0040-4020(01)81924-4"},{"doi-asserted-by":"publisher","key":"e_1_2_5_6_2","DOI":"10.1021\/jo960395y"},{"doi-asserted-by":"crossref","unstructured":"J. Quirante C. Escolano A. Merino J. Bonjoch J. Org. Chem.1998 63 968\u2013976 (and references cited therein).","key":"e_1_2_5_7_2","DOI":"10.1021\/jo971148c"},{"doi-asserted-by":"publisher","key":"e_1_2_5_8_2","DOI":"10.1016\/S0040-4039(99)00117-3"},{"doi-asserted-by":"publisher","key":"e_1_2_5_9_2","DOI":"10.1039\/a807930g"},{"doi-asserted-by":"publisher","key":"e_1_2_5_10_2","DOI":"10.1039\/p19920003165"},{"doi-asserted-by":"publisher","key":"e_1_2_5_11_2","DOI":"10.1055\/s-1997-704"},{"doi-asserted-by":"crossref","unstructured":"X. Du R. W. Armstrong Tetrahedron Lett.1998 39 2281\u20132284 (and references cited therein).","key":"e_1_2_5_12_2","DOI":"10.1016\/S0040-4039(98)00292-5"},{"doi-asserted-by":"publisher","key":"e_1_2_5_13_2","DOI":"10.1002\/ejoc.200200499"},{"doi-asserted-by":"crossref","unstructured":"S. Ozaki E. Matsui J. Waku H. Ohmori Tetrahedron Lett.1997 38 2705\u20132708 (and references cited therein).","key":"e_1_2_5_14_2","DOI":"10.1016\/S0040-4039(97)00434-6"},{"doi-asserted-by":"publisher","key":"e_1_2_5_15_2","DOI":"10.1021\/jo951653e"},{"doi-asserted-by":"crossref","unstructured":"S. Olivero J.\u2010P. Rolland E. Du\u00f1ach Organometallics1998 17 3747\u20133753 (and references cited therein).","key":"e_1_2_5_16_2","DOI":"10.1021\/om980247t"},{"doi-asserted-by":"publisher","key":"e_1_2_5_17_2","DOI":"10.1016\/0022-0728(92)80345-5"},{"key":"e_1_2_5_18_2","volume":"148","author":"Fang D. M.","year":"2001","journal-title":"J. Electrochem. Soc."},{"doi-asserted-by":"publisher","key":"e_1_2_5_19_2","DOI":"10.1016\/S0022-0728(00)00494-0"},{"doi-asserted-by":"publisher","key":"e_1_2_5_20_2","DOI":"10.1016\/S0040-4039(99)01845-6"},{"doi-asserted-by":"publisher","key":"e_1_2_5_21_2","DOI":"10.1021\/jo026102k"},{"doi-asserted-by":"publisher","key":"e_1_2_5_22_2","DOI":"10.1021\/np50073a023"},{"doi-asserted-by":"crossref","unstructured":"A. Merritt S. V. Ley Nat. Prod. Rep.1992 9 243\u2013287 (and references cited therein).","key":"e_1_2_5_23_2","DOI":"10.1039\/np9920900243"},{"doi-asserted-by":"publisher","key":"e_1_2_5_24_2","DOI":"10.1016\/j.jelechem.2003.07.011"},{"doi-asserted-by":"publisher","key":"e_1_2_5_25_2","DOI":"10.1039\/dt9780000972"},{"doi-asserted-by":"publisher","key":"e_1_2_5_26_2","DOI":"10.1016\/S0022-328X(00)80916-X"},{"doi-asserted-by":"publisher","key":"e_1_2_5_27_2","DOI":"10.1016\/S0022-328X(00)82420-1"},{"doi-asserted-by":"publisher","key":"e_1_2_5_28_2","DOI":"10.1016\/S0022-0728(81)80452-4"},{"doi-asserted-by":"publisher","key":"e_1_2_5_29_2","DOI":"10.1016\/S0022-0728(81)80453-6"},{"doi-asserted-by":"publisher","key":"e_1_2_5_30_2","DOI":"10.1021\/ja00048a021"},{"key":"e_1_2_5_31_2","first-page":"2410","volume":"49","author":"Petrov E. S.","year":"1979","journal-title":"Zh. Obshch. Khim."},{"doi-asserted-by":"publisher","key":"e_1_2_5_32_2","DOI":"10.1021\/ja00024a041"},{"doi-asserted-by":"publisher","key":"e_1_2_5_33_2","DOI":"10.1016\/S0040-4039(00)75801-1"},{"doi-asserted-by":"publisher","key":"e_1_2_5_34_2","DOI":"10.1039\/p19930002339"},{"doi-asserted-by":"publisher","key":"e_1_2_5_35_2","DOI":"10.1248\/cpb.43.32"},{"doi-asserted-by":"publisher","key":"e_1_2_5_36_2","DOI":"10.1021\/cr00032a008"},{"doi-asserted-by":"publisher","key":"e_1_2_5_37_2","DOI":"10.1021\/ja00531a023"},{"doi-asserted-by":"publisher","key":"e_1_2_5_38_2","DOI":"10.1021\/ja00532a023"},{"key":"e_1_2_5_39_2","first-page":"225","author":"Sav\u00e9ant J. M.","year":"1988","journal-title":"Bull. Soc. Chim. Fr."},{"doi-asserted-by":"publisher","key":"e_1_2_5_40_2","DOI":"10.1016\/0022-0728(95)03915-4"},{"volume-title":"Organic Electrochemistry","year":"2001","author":"Utley J. H. P.","key":"e_1_2_5_41_2"},{"volume-title":"March\u2019s Advanced Organic Chemistry","year":"2001","author":"Smith M. B.","key":"e_1_2_5_42_2"},{"doi-asserted-by":"publisher","key":"e_1_2_5_43_2","DOI":"10.1002\/9783527618293"},{"doi-asserted-by":"publisher","key":"e_1_2_5_44_2","DOI":"10.1021\/ic50030a004"},{"doi-asserted-by":"publisher","key":"e_1_2_5_45_2","DOI":"10.1016\/0022-0728(86)90030-6"},{"doi-asserted-by":"publisher","key":"e_1_2_5_46_2","DOI":"10.1021\/ac60251a014"},{"doi-asserted-by":"publisher","key":"e_1_2_5_47_2","DOI":"10.1016\/S0003-2670(01)81840-7"},{"doi-asserted-by":"publisher","key":"e_1_2_5_48_2","DOI":"10.1016\/0022-0728(85)85083-X"},{"doi-asserted-by":"publisher","key":"e_1_2_5_49_2","DOI":"10.1021\/ac00091a020"},{"doi-asserted-by":"publisher","key":"e_1_2_5_50_2","DOI":"10.1016\/0022-0728(94)03580-V"},{"doi-asserted-by":"publisher","key":"e_1_2_5_51_2","DOI":"10.1021\/jo00108a034"},{"doi-asserted-by":"publisher","key":"e_1_2_5_52_2","DOI":"10.1149\/1.1837304"}],"container-title":["European Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fejoc.200500478","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ejoc.200500478","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T22:21:57Z","timestamp":1760394117000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/ejoc.200500478"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2005,11]]},"references-count":52,"journal-issue":{"issue":"22","published-print":{"date-parts":[[2005,11]]}},"alternative-id":["10.1002\/ejoc.200500478"],"URL":"https:\/\/doi.org\/10.1002\/ejoc.200500478","archive":["Portico"],"relation":{},"ISSN":["1434-193X","1099-0690"],"issn-type":[{"type":"print","value":"1434-193X"},{"type":"electronic","value":"1099-0690"}],"subject":[],"published":{"date-parts":[[2005,11]]},"assertion":[{"value":"2005-06-28","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2005-11-03","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}