{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,23]],"date-time":"2026-08-23T14:06:17Z","timestamp":1787493977384,"version":"build-2736575974"},"reference-count":88,"publisher":"American Chemical Society (ACS)","issue":"20","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Org. Chem."],"published-print":{"date-parts":[[2011,10,21]]},"DOI":"10.1021\/jo2017923","type":"journal-article","created":{"date-parts":[[2011,9,6]],"date-time":"2011-09-06T19:03:54Z","timestamp":1315335834000},"page":"8447-8457","source":"Crossref","is-referenced-by-count":23,"title":["Oxidation of Annelated Diarylamines: Analysis of Reaction Pathways to Nitroxide Diradical and Spirocyclic Products"],"prefix":"10.1021","volume":"76","author":[{"given":"Andrzej","family":"Rajca","sequence":"first","affiliation":[{"name":"Department of Chemistry, University of Nebraska, Lincoln, Nebraska 68588-0304, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kouichi","family":"Shiraishi","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Nebraska, Lincoln, Nebraska 68588-0304, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Przemys\u0142aw J.","family":"Boraty\u0144ski","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Nebraska, Lincoln, Nebraska 68588-0304, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maren","family":"Pink","sequence":"additional","affiliation":[{"name":"IUMSC, Department of Chemistry, Indiana University, Bloomington, Indiana 47405-7102, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Makoto","family":"Miyasaka","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Nebraska, Lincoln, Nebraska 68588-0304, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Suchada","family":"Rajca","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Nebraska, Lincoln, Nebraska 68588-0304, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2011,9,21]]},"reference":[{"key":"ref1\/cit1","doi-asserted-by":"crossref","first-page":"971","DOI":"10.1070\/RC2009v078n11ABEH004093","volume":"78","author":"Tretyakov E. V.","year":"2009","journal-title":"Russ. Chem. Rev."},{"key":"ref2\/cit2","doi-asserted-by":"crossref","first-page":"980","DOI":"10.1021\/ol9029676","volume":"12","author":"Yamakoshi H.","year":"2010","journal-title":"Org. Lett."},{"key":"ref3\/cit3a","doi-asserted-by":"crossref","first-page":"836","DOI":"10.1039\/B818087C","author":"Koshika K.","year":"2009","journal-title":"Chem. Commun."},{"key":"ref3\/cit3b","doi-asserted-by":"crossref","first-page":"737","DOI":"10.1126\/science.1151831","volume":"319","author":"Nishide H.","year":"2008","journal-title":"Science"},{"key":"ref4\/cit4","doi-asserted-by":"crossref","first-page":"15908","DOI":"10.1021\/ja107769z","volume":"132","author":"Suzuki S.","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref5\/cit5","doi-asserted-by":"crossref","first-page":"3679","DOI":"10.1021\/jp056869r","volume":"110","author":"Goldstein S.","year":"2006","journal-title":"J. Phys. Chem. A"},{"key":"ref6\/cit6","doi-asserted-by":"crossref","first-page":"6463","DOI":"10.1021\/jo1011619","volume":"75","author":"Burks S. R.","year":"2010","journal-title":"J. Org. Chem."},{"key":"ref7\/cit7","doi-asserted-by":"crossref","first-page":"3661","DOI":"10.1021\/cr990119u","volume":"101","author":"Hawker C. J.","year":"2001","journal-title":"Chem. Rev."},{"key":"ref8\/cit8","doi-asserted-by":"crossref","first-page":"4356","DOI":"10.1021\/ja0576435","volume":"128","author":"Chernick E. T.","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref9\/cit9","doi-asserted-by":"crossref","first-page":"18304","DOI":"10.1021\/ja904648r","volume":"131","author":"Kirk M. L.","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"ref10\/cit10","doi-asserted-by":"crossref","first-page":"5778","DOI":"10.1002\/chem.200903102","volume":"16","author":"Rajca A.","year":"2010","journal-title":"Chem.\u2013Eur. J."},{"key":"ref11\/cit11a","unstructured":"Forrester, A. R.; Hay, J. M.; Thomson, R. H.Organic Chemistry of Stable Free Radicals;Academic Press:London, 1968; Chapter 5, pp180\u2013246."},{"key":"ref11\/cit11b","volume-title":"Synthetic Chemistry of Stable Nitroxides","author":"Volodarsky L. B.","year":"1994"},{"key":"ref12\/cit12","doi-asserted-by":"crossref","first-page":"4677","DOI":"10.1016\/S0040-4039(00)80578-X","volume":"29","author":"Murray R. W.","year":"1988","journal-title":"Tetrahedron Lett."},{"key":"ref13\/cit13","doi-asserted-by":"crossref","first-page":"10159","DOI":"10.1021\/ja0712017","volume":"129","author":"Rajca A.","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref14\/cit14a","doi-asserted-by":"crossref","first-page":"9099","DOI":"10.1021\/ja8016335","volume":"130","author":"Rajca A.","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref14\/cit14b","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1021\/jo702151n","volume":"73","author":"Vale M.","year":"2008","journal-title":"J. Org. Chem."},{"key":"ref15\/cit15","first-page":"2217","volume":"10","author":"Ivanov Y. A.","year":"1976","journal-title":"Izv. Akad. Nauk SSSR, Ser. Khim."},{"key":"ref16\/cit16","doi-asserted-by":"crossref","first-page":"9341","DOI":"10.1021\/jo0616299","volume":"71","author":"Delen Z.","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref17\/cit17","doi-asserted-by":"crossref","first-page":"581","DOI":"10.1016\/S0379-6779(02)00353-3","volume":"133","author":"Seino M.","year":"2003","journal-title":"Synth. Met."},{"key":"ref18\/cit18a","doi-asserted-by":"crossref","first-page":"4238","DOI":"10.1021\/ja00011a028","volume":"113","author":"Ishida T.","year":"1991","journal-title":"J. Am. Chem. Soc."},{"key":"ref18\/cit18b","doi-asserted-by":"crossref","first-page":"7168","DOI":"10.1021\/ja980817g","volume":"120","author":"Tanaka M.","year":"1998","journal-title":"J. Am. Chem. Soc."},{"key":"ref18\/cit18c","doi-asserted-by":"crossref","first-page":"1209","DOI":"10.1039\/B610365K","volume":"17","author":"Oka H.","year":"2007","journal-title":"J. Mater. Chem."},{"key":"ref19\/cit19","doi-asserted-by":"crossref","first-page":"4372","DOI":"10.1039\/b909741d","author":"Rajca A.","year":"2009","journal-title":"Chem. Commun."},{"key":"ref20\/cit20","doi-asserted-by":"crossref","first-page":"4709","DOI":"10.1039\/c0cp01878c","volume":"13","author":"Barone V.","year":"2011","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref21\/cit21a","doi-asserted-by":"crossref","first-page":"3682","DOI":"10.1021\/ja910483b","volume":"132","author":"Herrmann C.","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref21\/cit21b","doi-asserted-by":"crossref","first-page":"3700","DOI":"10.1021\/ja808924f","volume":"131","author":"Giacobbe E. M.","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"ref21\/cit21c","doi-asserted-by":"crossref","first-page":"4528","DOI":"10.1021\/ja9109538","volume":"132","author":"Komatsu H.","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref22\/cit22a","doi-asserted-by":"crossref","first-page":"1760","DOI":"10.1021\/jo00032a030","volume":"57","author":"Rajca A.","year":"1992","journal-title":"J. Org. Chem."},{"key":"ref22\/cit22b","doi-asserted-by":"crossref","first-page":"7232","DOI":"10.1021\/ja071881d","volume":"129","author":"Rajca A.","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref22\/cit22c","doi-asserted-by":"crossref","first-page":"5459","DOI":"10.1002\/anie.201002811","volume":"49","author":"Boraty\u0144ski P. J.","year":"2010","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref23\/cit23a","doi-asserted-by":"crossref","first-page":"346","DOI":"10.1021\/ar00030a008","volume":"26","author":"Iwamura H.","year":"1993","journal-title":"Acc. Chem. Res."},{"key":"ref23\/cit23b","doi-asserted-by":"crossref","first-page":"871","DOI":"10.1021\/cr00028a002","volume":"94","author":"Rajca A.","year":"1994","journal-title":"Chem. Rev."},{"key":"ref23\/cit23c","unstructured":"Magnetic Properties of Organic Materials;Lahti, P. M., Ed.Marcel Dekker:New York, 1999; pp1\u2013713."},{"key":"ref23\/cit23d","unstructured":"Molecular Magnetism;Itoh, K.; Kinoshita, M., Eds.Gordon and Breach:Kodansha, 2000; pp1\u2013337."},{"key":"ref23\/cit23e","doi-asserted-by":"crossref","first-page":"4834","DOI":"10.1002\/1521-3765(20021104)8:21<4834::AID-CHEM4834>3.0.CO;2-E","volume":"8","author":"Rajca A.","year":"2002","journal-title":"Chem.\u2014Eur. J."},{"key":"ref23\/cit23f","first-page":"153","volume":"40","author":"Rajca A.","year":"2005","journal-title":"Adv. Phys. Org. Chem."},{"key":"ref23\/cit23g","doi-asserted-by":"crossref","first-page":"863","DOI":"10.1070\/RC2006v075n10ABEH003621","volume":"75","author":"Shishlov N. M.","year":"2006","journal-title":"Russ. Chem. Rev."},{"key":"ref24\/cit24a","doi-asserted-by":"crossref","first-page":"1503","DOI":"10.1126\/science.1065477","volume":"294","author":"Rajca A.","year":"2001","journal-title":"Science"},{"key":"ref24\/cit24b","doi-asserted-by":"crossref","first-page":"6308","DOI":"10.1021\/ja990881d","volume":"121","author":"Rajca A.","year":"1999","journal-title":"J. Am. Chem. Soc."},{"key":"ref25\/cit25a","doi-asserted-by":"crossref","first-page":"6972","DOI":"10.1021\/ja031548j","volume":"126","author":"Rajca S.","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref25\/cit25b","doi-asserted-by":"crossref","first-page":"6608","DOI":"10.1021\/ja031549b","volume":"126","author":"Rajca A.","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref25\/cit25c","doi-asserted-by":"crossref","first-page":"3144","DOI":"10.1002\/chem.200306036","volume":"10","author":"Rajca A.","year":"2004","journal-title":"Chem.\u2014Eur. J."},{"key":"ref25\/cit25d","doi-asserted-by":"crossref","first-page":"10335","DOI":"10.1021\/ja971493j","volume":"119","author":"Rajca A.","year":"1997","journal-title":"J. Am. Chem. Soc."},{"key":"ref25\/cit25e","doi-asserted-by":"crossref","first-page":"2091","DOI":"10.1002\/anie.199420911","volume":"33","author":"Rajca A.","year":"1994","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ref25\/cit25f","doi-asserted-by":"crossref","first-page":"5890","DOI":"10.1021\/ja00171a045","volume":"112","author":"Rajca A.","year":"1990","journal-title":"J. Am. Chem. Soc."},{"key":"ref25\/cit25g","doi-asserted-by":"crossref","first-page":"5889","DOI":"10.1021\/ja00171a044","volume":"112","author":"Rajca A.","year":"1990","journal-title":"J. Am. Chem. Soc."},{"key":"ref26\/cit26","doi-asserted-by":"crossref","first-page":"9312","DOI":"10.1021\/ja051521v","volume":"127","author":"Shiraishi K.","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref28\/cit28","doi-asserted-by":"crossref","first-page":"4017","DOI":"10.1021\/jo900482q","volume":"74","author":"Jain R.","year":"2009","journal-title":"J. Org. Chem."},{"key":"ref29\/cit29","doi-asserted-by":"crossref","first-page":"6072","DOI":"10.1021\/ja201108a","volume":"133","author":"Saielli G.","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"ref30\/cit30","doi-asserted-by":"crossref","first-page":"326","DOI":"10.1021\/ar800163d","volume":"42","author":"Jacquemin D.","year":"2009","journal-title":"Acc. Chem. Res."},{"key":"ref31\/cit31","doi-asserted-by":"crossref","first-page":"12267","DOI":"10.1021\/jp0643303","volume":"110","author":"Sinnecker S.","year":"2006","journal-title":"J. Phys. Chem. A"},{"key":"ref32\/cit32","doi-asserted-by":"crossref","first-page":"11080","DOI":"10.1063\/1.1419058","volume":"115","author":"Neese F.","year":"2001","journal-title":"J. Chem. Phys."},{"key":"ref33\/cit33","doi-asserted-by":"crossref","first-page":"7990","DOI":"10.1002\/chem.200802443","volume":"15","author":"Rastrelli F.","year":"2009","journal-title":"Chem.\u2013Eur. J."},{"key":"ref34\/cit34","doi-asserted-by":"crossref","first-page":"4750","DOI":"10.1021\/ja200708b","volume":"133","author":"Rajca A.","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"ref35\/cit35","doi-asserted-by":"crossref","first-page":"6443","DOI":"10.1039\/c1cc11172h","volume":"47","author":"Olankitwanit A.","year":"2011","journal-title":"Chem. Commun."},{"key":"ref36\/cit36a","unstructured":"Frisch, M. J.Gaussian 03, Revision E.01;Gaussian:Wallingford, CT, 2004."},{"key":"ref36\/cit36b","unstructured":"Frisch, M. J.Gaussian 09, Revision A.01;Gaussian:Wallingford, CT, 2009."},{"key":"ref37\/cit37a","unstructured":"Neese, F.ORCA\u2014an ab initio, density functional and semiempirical program package, Version 2.6;University of Bonn:Bonn, 2008."},{"key":"ref37\/cit37b","doi-asserted-by":"crossref","first-page":"174","DOI":"10.1002\/jcc.21600","volume":"32","author":"Allouche A.-R.","year":"2011","journal-title":"J. Comput. Chem."},{"key":"ref38\/cit38","doi-asserted-by":"crossref","first-page":"13497","DOI":"10.1021\/ja063567+","volume":"128","author":"Rajca A.","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref39\/cit39","doi-asserted-by":"crossref","first-page":"4381","DOI":"10.1021\/ja00947a028","volume":"87","author":"Russell G. A.","year":"1965","journal-title":"J. Am. Chem. Soc."},{"key":"ref41\/cit41","doi-asserted-by":"crossref","first-page":"5014","DOI":"10.1021\/ja01575a050","volume":"79","author":"Pedersen C. J.","year":"1957","journal-title":"J. Am. Chem. Soc."},{"key":"ref42\/cit42","first-page":"73","volume-title":"Organic Reactions","volume":"9","author":"Hassal C. H.","year":"1957"},{"key":"ref43\/cit43","doi-asserted-by":"crossref","first-page":"251","DOI":"10.1002\/0471264180.or043.03","volume-title":"Organic Reactions","volume":"43","author":"Krow G. R.","year":"1993"},{"key":"ref44\/cit44","doi-asserted-by":"crossref","first-page":"1153","DOI":"10.1021\/jo01294a047","volume":"45","author":"Demmin T. R.","year":"1980","journal-title":"J. Org. Chem."},{"key":"ref45\/cit45","doi-asserted-by":"crossref","first-page":"1525","DOI":"10.1002\/cber.19580910724","volume":"91","author":"Alder K.","year":"1958","journal-title":"Chem. Ber."},{"key":"ref46\/cit46","doi-asserted-by":"crossref","first-page":"5635","DOI":"10.1016\/j.bmc.2008.03.073","volume":"16","author":"Yang R.-Y.","year":"2008","journal-title":"Bioorg. Med. Chem."},{"key":"ref48\/cit48","doi-asserted-by":"crossref","first-page":"2548","DOI":"10.1021\/jo01270a097","volume":"33","author":"Richmond R. J.","year":"1968","journal-title":"J. Org. Chem."},{"key":"ref49\/cit49","doi-asserted-by":"crossref","first-page":"2186","DOI":"10.1002\/hlca.19840670820","volume":"67","author":"Adam J. M.","year":"1984","journal-title":"Helv. Chim. Acta"},{"key":"ref50\/cit50a","unstructured":"As neither8Anor8Bare isolated, computational determination of the kinetically-controlled regioselectivity between8Aand8Bwould be prohibitive given the size and complexity of the present system and the expected small free energy differences between the relevant transition states."},{"key":"ref50\/cit50b","doi-asserted-by":"crossref","first-page":"861","DOI":"10.1021\/jo0513966","volume":"71","author":"Grein F.","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref51\/cit51","doi-asserted-by":"crossref","first-page":"121","DOI":"10.1039\/P29800000121","author":"Brady K.","year":"1980","journal-title":"J. Chem. Soc, Perkin Trans. 2"},{"key":"ref52\/cit52a","doi-asserted-by":"crossref","first-page":"1869","DOI":"10.1016\/S0040-4039(00)90143-6","volume":"23","author":"Curtin D. Y.","year":"1965","journal-title":"Tetrahedron Lett."},{"key":"ref52\/cit52b","doi-asserted-by":"crossref","first-page":"637","DOI":"10.1021\/ja00979a030","volume":"89","author":"Curtin D. Y.","year":"1967","journal-title":"J. Am. Chem. Soc."},{"key":"ref53\/cit53a","doi-asserted-by":"crossref","first-page":"5582","DOI":"10.1021\/ja00852a044","volume":"97","author":"Kukolja S.","year":"1975","journal-title":"J. Am. Chem. Soc."},{"key":"ref53\/cit53b","doi-asserted-by":"crossref","first-page":"3437","DOI":"10.1002\/ejoc.201100148","author":"Crauste C.","year":"2011","journal-title":"Eur. J. Org. Chem."},{"key":"ref54\/cit54","doi-asserted-by":"crossref","first-page":"3024","DOI":"10.1021\/jo7023834","volume":"73","author":"Wiitala K. W.","year":"2008","journal-title":"J. Org. Chem."},{"key":"ref55\/cit55","doi-asserted-by":"crossref","first-page":"3182","DOI":"10.1016\/j.tetlet.2009.01.121","volume":"50","author":"Stockdill J. L.","year":"2009","journal-title":"Tetrahedron Lett."},{"key":"ref56\/cit56","doi-asserted-by":"crossref","first-page":"971","DOI":"10.1070\/RC2001v070n11ABEH000642","volume":"70","author":"Banerjee A. K.","year":"2001","journal-title":"Russ. Chem. Rev."},{"key":"ref57\/cit57","doi-asserted-by":"crossref","first-page":"1867","DOI":"10.1021\/jo062670e","volume":"72","author":"Spagnol G.","year":"2007","journal-title":"J. Org. Chem."},{"key":"ref58\/cit58a","doi-asserted-by":"crossref","first-page":"383","DOI":"10.1039\/c29710000383","author":"Chapman O. L.","year":"1971","journal-title":"J. Chem. Soc., Chem. Commun."},{"key":"ref58\/cit58b","doi-asserted-by":"crossref","first-page":"1365","DOI":"10.1021\/ja00759a060","volume":"94","author":"Chapman O. L.","year":"1972","journal-title":"J. Am. Chem. Soc."},{"key":"ref60\/cit60","doi-asserted-by":"crossref","first-page":"2999","DOI":"10.1021\/cr9904009","volume":"105","author":"Tomasi J.","year":"2005","journal-title":"Chem. Rev."},{"key":"ref61\/cit61","doi-asserted-by":"crossref","first-page":"3233","DOI":"10.1002\/1521-3765(20020715)8:14<3233::AID-CHEM3233>3.0.CO;2-0","volume":"8","author":"Barone G.","year":"2002","journal-title":"Chem.\u2014Eur. J."},{"key":"ref62\/cit62","doi-asserted-by":"crossref","first-page":"1187","DOI":"10.1021\/jo802370v","volume":"74","author":"Nielsen D. K.","year":"2009","journal-title":"J. Org. Chem."},{"key":"ref63\/cit63a","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/3-540-56252-4_22","volume":"164","author":"Heaney H.","year":"1993","journal-title":"Top. Curr. Chem."},{"key":"ref63\/cit63b","unstructured":"Technical Bulletin AL-116, 1996, http:\/\/www.sigmaaldrich.com\/etc\/medialib\/docs\/Aldrich\/Bulletin\/al_techbull_al116.Par.0001.File.tmp\/al_techbull_al116.pdf(accessed on Aug. 28, 2011)."}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jo2017923","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,4,22]],"date-time":"2023-04-22T00:50:52Z","timestamp":1682124652000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/jo2017923"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2011,9,21]]},"references-count":88,"journal-issue":{"issue":"20","published-print":{"date-parts":[[2011,10,21]]}},"alternative-id":["10.1021\/jo2017923"],"URL":"https:\/\/doi.org\/10.1021\/jo2017923","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2011,9,21]]}}}