{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,4]],"date-time":"2026-10-04T04:24:38Z","timestamp":1791087878221,"version":"4.1.0"},"reference-count":57,"publisher":"American Chemical Society (ACS)","issue":"22","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Org. Chem."],"published-print":{"date-parts":[[2011,11,18]]},"DOI":"10.1021\/jo201668w","type":"journal-article","created":{"date-parts":[[2011,10,19]],"date-time":"2011-10-19T20:37:14Z","timestamp":1319056634000},"page":"9391-9408","source":"Crossref","is-referenced-by-count":43,"title":["Electrophilicities of Symmetrically Substituted 1,3-Diarylallyl Cations"],"prefix":"10.1021","volume":"76","author":[{"given":"Konstantin","family":"Troshin","sequence":"first","affiliation":[{"name":"Department Chemie, Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen, Butenandtstrasse 5-13 (Haus F), 81377 M\u00fcnchen, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claus","family":"Schindele","sequence":"additional","affiliation":[{"name":"Department Chemie, Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen, Butenandtstrasse 5-13 (Haus F), 81377 M\u00fcnchen, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Herbert","family":"Mayr","sequence":"additional","affiliation":[{"name":"Department Chemie, Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen, Butenandtstrasse 5-13 (Haus F), 81377 M\u00fcnchen, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2011,10,19]]},"reference":[{"key":"ref1\/cit1a","doi-asserted-by":"crossref","first-page":"753","DOI":"10.1021\/cr50010a002","volume":"56","author":"DeWolfe R. H.","year":"1956","journal-title":"Chem. Rev."},{"key":"ref1\/cit1b","doi-asserted-by":"crossref","first-page":"1901","DOI":"10.1016\/0040-4020(80)80203-1","volume":"36","author":"Magid R. M.","year":"1980","journal-title":"Tetrahedron"},{"key":"ref1\/cit1c","doi-asserted-by":"crossref","first-page":"1503","DOI":"10.1021\/cr00097a006","volume":"89","author":"Marshall J. A.","year":"1989","journal-title":"Chem. Rev."},{"key":"ref2\/cit2a","doi-asserted-by":"crossref","first-page":"281","DOI":"10.1021\/ar50033a001","volume":"3","author":"Bordwell F. G.","year":"1970","journal-title":"Acc. Chem. Res."},{"key":"ref2\/cit2b","doi-asserted-by":"crossref","first-page":"5829","DOI":"10.1021\/ja00771a048","volume":"94","author":"Bordwell F. G.","year":"1972","journal-title":"J. Am. Chem. Soc."},{"key":"ref3\/cit3a","doi-asserted-by":"crossref","first-page":"3240","DOI":"10.1021\/jo01272a044","volume":"33","author":"Bordwell F. G.","year":"1968","journal-title":"J. Org. Chem."},{"key":"ref3\/cit3b","doi-asserted-by":"crossref","first-page":"5825","DOI":"10.1021\/ja00771a047","volume":"94","author":"Bordwell F. G.","year":"1972","journal-title":"J. Am. Chem. Soc."},{"key":"ref4\/cit4","doi-asserted-by":"crossref","first-page":"6469","DOI":"10.1021\/ja00488a034","volume":"100","author":"Goering H. L.","year":"1978","journal-title":"J. Am. Chem. Soc."},{"key":"ref5\/cit5a","doi-asserted-by":"crossref","first-page":"2641","DOI":"10.1021\/ja045562n","volume":"127","author":"Minegishi S.","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref5\/cit5b","doi-asserted-by":"crossref","first-page":"667","DOI":"10.1351\/PAC-CON-08-08-26","volume":"81","author":"Mayr H.","year":"2009","journal-title":"Pure Appl. Chem."},{"key":"ref6\/cit6","doi-asserted-by":"crossref","first-page":"11392","DOI":"10.1021\/ja903207b","volume":"131","author":"Phan T. B.","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"ref7\/cit7","doi-asserted-by":"crossref","first-page":"3612","DOI":"10.1002\/anie.201007923","volume":"50","author":"Mayr H.","year":"2011","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref8\/cit8a","doi-asserted-by":"crossref","first-page":"9500","DOI":"10.1021\/ja010890y","volume":"123","author":"Mayr H.","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"ref8\/cit8b","doi-asserted-by":"crossref","first-page":"91","DOI":"10.1002\/1521-3773(20020104)41:1<91::AID-ANIE91>3.0.CO;2-P","volume":"41","author":"Lucius R.","year":"2002","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref8\/cit8c","doi-asserted-by":"crossref","first-page":"66","DOI":"10.1021\/ar020094c","volume":"36","author":"Mayr H.","year":"2003","journal-title":"Acc. Chem. Res."},{"key":"ref9\/cit9a","doi-asserted-by":"crossref","first-page":"11208","DOI":"10.1021\/ja020617b","volume":"124","author":"Schindele C.","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref9\/cit9b","doi-asserted-by":"crossref","first-page":"2586","DOI":"10.1002\/chem.200902484","volume":"16","author":"Wang C.","year":"2010","journal-title":"Chem.\u2014Eur. J."},{"key":"ref9\/cit9c","doi-asserted-by":"crossref","first-page":"139","DOI":"10.1016\/S1380-7323(07)80010-0","volume":"19","author":"Perez P.","year":"2007","journal-title":"Theor. Comput. Chem."},{"key":"ref10\/cit10","unstructured":"For a database of reactivity parametersE,N, andsN:www.cup.lmu.de\/oc\/mayr\/DBintro.html."},{"key":"ref11\/cit11a","doi-asserted-by":"crossref","first-page":"395","DOI":"10.1021\/cr9409804","volume":"96","author":"Trost B. M.","year":"1996","journal-title":"Chem. Rev."},{"key":"ref11\/cit11b","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1248\/cpb.50.1","volume":"50","author":"Trost B. M.","year":"2002","journal-title":"Chem. Pharm. Bull."},{"key":"ref11\/cit11c","doi-asserted-by":"crossref","first-page":"2921","DOI":"10.1021\/cr020027w","volume":"103","author":"Trost B. M.","year":"2003","journal-title":"Chem. Rev."},{"key":"ref12\/cit12","doi-asserted-by":"crossref","first-page":"647","DOI":"10.1002\/ejoc.201001474","author":"Emer E.","year":"2011","journal-title":"Eur. J. Org. Chem."},{"key":"ref13\/cit13","doi-asserted-by":"crossref","first-page":"1719","DOI":"10.1021\/ma9024569","volume":"43","author":"Ammer J.","year":"2010","journal-title":"Macromolecules"},{"key":"ref14\/cit14","volume-title":"Introduction to NMR Spectroscopy","author":"Abraham R. J.","year":"1988"},{"key":"ref15\/cit15","unstructured":"CCDC 297424 contains the supplementary crystallographic data for1h-BF4reported in this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk\/data_request\/cif."},{"key":"ref16\/cit16","doi-asserted-by":"crossref","first-page":"1841","DOI":"10.1002\/adsc.200606183","volume":"348","author":"Sanz R.","year":"2006","journal-title":"Adv. Synth. Catal."},{"key":"ref17\/cit17","doi-asserted-by":"crossref","first-page":"345","DOI":"10.1021\/ar50106a001","volume":"9","author":"Rys P.","year":"1976","journal-title":"Acc. Chem. Res."},{"key":"ref18\/cit18a","doi-asserted-by":"crossref","first-page":"4446","DOI":"10.1021\/ja00167a049","volume":"112","author":"Mayr H.","year":"1990","journal-title":"J. Am. Chem. Soc."},{"key":"ref18\/cit18b","doi-asserted-by":"crossref","first-page":"4954","DOI":"10.1021\/ja00013a035","volume":"113","author":"Hagen G.","year":"1991","journal-title":"J. Am. Chem. Soc."},{"key":"ref20\/cit20","doi-asserted-by":"crossref","first-page":"2418","DOI":"10.1021\/ja982072k","volume":"121","author":"Mayr H.","year":"1999","journal-title":"J. Am. Chem. Soc."},{"key":"ref21\/cit21","doi-asserted-by":"crossref","first-page":"1435","DOI":"10.1039\/B203554E","author":"Mayr H.","year":"2002","journal-title":"J. Chem. Soc., Perkin Trans. 2"},{"key":"ref22\/cit22","first-page":"961","author":"Nubbemeyer U.","year":"2003","journal-title":"Synthesis"},{"key":"ref23\/cit23","doi-asserted-by":"crossref","first-page":"5724","DOI":"10.1021\/jp9814449","volume":"102","author":"Miranda M. A.","year":"1998","journal-title":"J. Phys. Chem. A"},{"key":"ref24\/cit24","doi-asserted-by":"crossref","first-page":"5174","DOI":"10.1021\/ja031828z","volume":"126","author":"Minegishi S.","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref25\/cit25","doi-asserted-by":"crossref","first-page":"165","DOI":"10.1021\/cr00002a004","volume":"91","author":"Hansch C.","year":"1991","journal-title":"Chem. Rev."},{"key":"ref26\/cit26","doi-asserted-by":"crossref","first-page":"291","DOI":"10.1002\/jcc.20790","volume":"29","author":"Wei Y.","year":"2008","journal-title":"J. Comput. Chem."},{"key":"ref27\/cit27","doi-asserted-by":"crossref","first-page":"7478","DOI":"10.1002\/chem.200902670","volume":"16","author":"Horn M.","year":"2010","journal-title":"Chem.\u2014Eur. J."},{"key":"ref28\/cit28a","doi-asserted-by":"crossref","first-page":"228","DOI":"10.1055\/s-1984-30782","author":"Olah G. A.","year":"1984","journal-title":"Synthesis"},{"key":"ref28\/cit28b","unstructured":"Samples taken from the reaction mixture were quenched with a solution of iodine in THF. The resulting mixture was dissolved in diethyl ether, washed with aqueous sodium thiosulfate solution, and dried (MgSO4). GC\u2013MS analysis showed slow disappearance of 1-bromo-3,5-difluorobenzene while the peak of the product of the reaction of the in situ generated (3,5-difluorophenyl)magnesium chloride with iodine, that is, 1,3-difluoro-5-iodobenzene, increased with time."},{"key":"ref29\/cit29","unstructured":"SDBSWeb:http:\/\/riodb01.ibase.aist.go.jp\/sdbs\/(National Institute of Advanced Industrial Science and Technology, 26.10.2010), SDBS No. 41165, Spectral Code HR2002-00194TS."},{"key":"ref30\/cit30","doi-asserted-by":"crossref","first-page":"696","DOI":"10.1021\/jo01319a007","volume":"44","author":"Jones P. R.","year":"1979","journal-title":"J. Org. Chem."},{"key":"ref31\/cit31","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1002\/ardp.200390010","volume":"336","author":"Manolov I.","year":"2003","journal-title":"Arch. Pharm."},{"key":"ref32\/cit32","doi-asserted-by":"crossref","first-page":"1179","DOI":"10.1039\/p19900001179","author":"Dickinson J. M.","year":"1990","journal-title":"J. Chem. Soc., Perkin Trans. 1"},{"key":"ref33\/cit33","doi-asserted-by":"crossref","first-page":"6301","DOI":"10.1021\/ja00198a048","volume":"111","author":"Hayashi T.","year":"1989","journal-title":"J. Am. Chem. Soc."},{"key":"ref34\/cit34","doi-asserted-by":"crossref","first-page":"283","DOI":"10.1002\/jlac.198819880402","author":"Quinkert G.","year":"1988","journal-title":"Liebigs Ann. Chem."},{"key":"ref35\/cit35","doi-asserted-by":"crossref","first-page":"1387","DOI":"10.1021\/jo005698d","volume":"66","author":"Nudelman N. S.","year":"2001","journal-title":"J. Org. Chem."},{"key":"ref36\/cit36","doi-asserted-by":"crossref","first-page":"525","DOI":"10.1007\/BF00524869","volume":"11","author":"Pivnenko N. S.","year":"1976","journal-title":"Theor. Exp. Chem"},{"key":"ref37\/cit37","doi-asserted-by":"crossref","first-page":"363","DOI":"10.1002\/cber.19701030206","volume":"103","author":"Brieskorn C.-H.","year":"1970","journal-title":"Chem. Ber."},{"key":"ref38\/cit38","unstructured":"Aizensutatsuto, A.; Haamorin, J.Jpn. Kokai Tokkyo Koho 1993, JP 05221932."},{"key":"ref39\/cit39","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1016\/j.tet.2006.10.044","volume":"63","author":"Wang H.","year":"2007","journal-title":"Tetrahedron"},{"key":"ref40\/cit40","doi-asserted-by":"crossref","first-page":"777","DOI":"10.1021\/ol034071p","volume":"5","author":"Battistuzzi G.","year":"2003","journal-title":"Org. Lett."},{"key":"ref41\/cit41","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1016\/j.dyepig.2008.12.010","volume":"82","author":"Coe B. J.","year":"2009","journal-title":"Dyes Pigm."},{"key":"ref42\/cit42","doi-asserted-by":"crossref","first-page":"2473","DOI":"10.1002\/cber.19861190808","volume":"119","author":"Mayr H.","year":"1986","journal-title":"Chem. Ber."},{"key":"ref43\/cit43","doi-asserted-by":"crossref","first-page":"1126","DOI":"10.1021\/ol1031552","volume":"13","author":"Liu Y.","year":"2011","journal-title":"Org. Lett."},{"key":"ref44\/cit44","doi-asserted-by":"crossref","first-page":"6379","DOI":"10.1002\/ejoc.200900925","author":"Kanzian T.","year":"2009","journal-title":"Eur. J. Org. Chem."},{"key":"ref45\/cit45","doi-asserted-by":"crossref","first-page":"12980","DOI":"10.1021\/ja036838e","volume":"125","author":"Bug T.","year":"2003","journal-title":"J. Am. Chem. Soc."}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jo201668w","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,4,4]],"date-time":"2023-04-04T03:26:38Z","timestamp":1680578798000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/jo201668w"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2011,10,19]]},"references-count":57,"journal-issue":{"issue":"22","published-print":{"date-parts":[[2011,11,18]]}},"alternative-id":["10.1021\/jo201668w"],"URL":"https:\/\/doi.org\/10.1021\/jo201668w","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2011,10,19]]}}}