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L. and Gao, D.InElectron Transfer in Chemistry;Balzani, V., Ed.Wiley-VCH:Weinheim, 2001; Vol.2(see especially pp141\u2212172)."},{"key":"ref1\/cit1b","doi-asserted-by":"crossref","first-page":"6730","DOI":"10.1021\/ja983993y","volume":"121","author":"Haberl U.","year":"1999","journal-title":"J. Am. Chem. Soc."},{"key":"ref1\/cit1c","doi-asserted-by":"crossref","first-page":"718","DOI":"10.1021\/ja00393a061","volume":"103","author":"Bellville D. J.","year":"1981","journal-title":"J. Am. Chem. Soc."},{"key":"ref2\/cit2a","doi-asserted-by":"crossref","first-page":"12414","DOI":"10.1021\/ja076172e","volume":"129","author":"Tang F.","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref2\/cit2b","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1007\/3-540-61454-0_70","volume":"185","author":"Moeller K. D.","year":"1997","journal-title":"Top. Curr. 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Rev."},{"key":"ref5\/cit5b","volume-title":"Synthetic Organic Electrochemistry","author":"Fry A. J.","year":"1989"},{"key":"ref6\/cit6","doi-asserted-by":"crossref","first-page":"13542","DOI":"10.1021\/ja806259z","volume":"130","author":"Xu H.-C.","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref7\/cit7a","doi-asserted-by":"crossref","first-page":"2692","DOI":"10.1021\/ja710513n","volume":"130","author":"Chong D.","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref7\/cit7b","doi-asserted-by":"crossref","first-page":"15676","DOI":"10.1021\/ja055045k","volume":"127","author":"Chong D.","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref8\/cit8","unstructured":"Photolytic preparations:"},{"key":"ref8\/cit8a","doi-asserted-by":"crossref","first-page":"1419","DOI":"10.1016\/S0040-4039(00)81671-8","volume":"24","author":"Timmermans P. J. J. A.","year":"1983","journal-title":"Tetrahedron Lett."},{"key":"ref8\/cit8b","doi-asserted-by":"crossref","first-page":"1311","DOI":"10.1016\/0040-4020(82)85119-3","volume":"38","author":"Spee T.","year":"1982","journal-title":"Tetrahedron"},{"key":"ref8\/cit8c","doi-asserted-by":"crossref","first-page":"1145","DOI":"10.1021\/ja00811a031","volume":"96","author":"Salmon R. G.","year":"1974","journal-title":"J. Am. Chem. Soc."},{"key":"ref8\/cit8d","doi-asserted-by":"crossref","first-page":"1303","DOI":"10.1016\/0040-4020(82)85118-1","volume":"38","author":"Leitch J.","year":"1982","journal-title":"Tetrahedron"},{"key":"ref9\/cit9a","doi-asserted-by":"crossref","first-page":"5950","DOI":"10.1021\/jo980601x","volume":"63","author":"Yoshida J.","year":"1998","journal-title":"J. Org. Chem."},{"key":"ref9\/cit9b","doi-asserted-by":"crossref","first-page":"923","DOI":"10.1016\/0013-4686(78)87016-9","volume":"23","author":"Campbell C. B.","year":"1978","journal-title":"Electrochim. Acta"},{"key":"ref9\/cit9c","doi-asserted-by":"crossref","first-page":"133","DOI":"10.1016\/S0022-0728(73)80083-X","volume":"42","author":"Clark D. B.","year":"1973","journal-title":"J. Electroanal. Chem."},{"key":"ref10\/cit10","unstructured":"See, for example:"},{"key":"ref10\/cit10a","doi-asserted-by":"crossref","first-page":"9859","DOI":"10.1021\/ja801930q","volume":"130","author":"Laws D. R.","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref10\/cit10b","doi-asserted-by":"crossref","first-page":"7260","DOI":"10.1021\/ja012641f","volume":"124","author":"Camire N.","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref11\/cit11a","doi-asserted-by":"crossref","first-page":"323","DOI":"10.1021\/ja00496a008","volume":"101","author":"Robinson J.","year":"1979","journal-title":"J. Am. Chem. Soc."},{"key":"ref12\/cit12a","unstructured":"aBard, A. J. and Faulkner, L. R.Electrochemical Methods, 2nd ed.John Wiley & Sons:New York, 2001; pp471\u2212475."},{"key":"ref12\/cit12b","unstructured":"bKissinger, P. T., Preddy, C. R., Shoup, R. E., and Heineman, W. R.InLaboratory Techniques in Electroanalytical Chemistry, 2nd ed.Kissinger, P. T. and Heineman, W. R., Eds.Marcel Dekker:New York, 1996; p40."},{"key":"ref13\/cit13","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1016\/0022-0728(91)85207-6","volume":"305","author":"Denuault G.","year":"1991","journal-title":"J. Electroanal. Chem."},{"key":"ref14\/cit14","unstructured":"Typical conditions: 6.7 mg (20 \u03bcmol) of1and 54 mg (500 \u03bcmol) of COE in 10 mL of 0.1 M [NBu4][TFAB]\/CH2Cl2under nitrogen; electrolyze at 293 K for 15 min; add 30 mL of hexanes to precipitate supporting electrolyte; filter, evaporate, extract, and elute with hexane through activated alumina, affording 43 mg of an oil shown to be a mixture of2and its diastereomers."},{"key":"ref15\/cit15","unstructured":"Saturn 2100T with CP8944 column, methanol chemical ionization."},{"key":"ref16\/cit16","unstructured":"Longer electrolysis times result in some conversion of the rhenium catalyst to 18-electron addition products [ReCp(CO)3X]+(X = H, Cl),7abut the original complex1may be regenerated by cathodic reduction of those side products."},{"key":"ref17\/cit17","unstructured":"The bracketed intermediate in Scheme2is meant to convey that the ET step may follow either an inner- or outer-sphere pathway. Although the former would be consistent with the ability of the Re complex to adopt seven-coordination,7the latter is supported by the fact that some oxidation ofcis-COE was found to be catalyzed by the aminium ET mediator1,3,4[N(C6H3Br2)3]+. Although the aminium ion is also a strong one-electron oxidant (E1\/2= 1.1 V in this medium), it lacks a metal center capable of expanding its coordination sphere. Compared to the Re-catalyzed process, the aminium-catalyzed reaction proceeds at a slower rate and gives greater product diversity. Detailed comparisons are under investigation."},{"key":"ref18\/cit18","unstructured":"The cyclized radical cation formed in eq 2 is a stronger oxidant than the radical cation of the olefin substrate. See ref 1a, pp163\u2212165."}],"container-title":["Journal of the American Chemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ja9032296","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,9]],"date-time":"2023-03-09T03:17:52Z","timestamp":1678331872000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ja9032296"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,5,22]]},"references-count":34,"journal-issue":{"issue":"23","published-print":{"date-parts":[[2009,6,17]]}},"alternative-id":["10.1021\/ja9032296"],"URL":"https:\/\/doi.org\/10.1021\/ja9032296","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2009,5,22]]}}}