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C.","year":"1992","journal-title":"J. Am. Chem. Soc."},{"key":"ref18\/cit18a","doi-asserted-by":"crossref","first-page":"5879","DOI":"10.1039\/b512117e","author":"Ashkenazi N.","year":"2005","journal-title":"Chem. Commun."},{"key":"ref18\/cit18b","doi-asserted-by":"crossref","first-page":"420","DOI":"10.1080\/10426500701735452","volume":"183","author":"Ashkenazi N.","year":"2008","journal-title":"Phosphorus, Sulfur, Silicon Relat. Elem."},{"key":"ref19\/cit19a","doi-asserted-by":"crossref","first-page":"1102","DOI":"10.1021\/ja01466a025","volume":"83","author":"Haake P. C.","year":"1961","journal-title":"J. Am. Chem. Soc."},{"key":"ref19\/cit19b","doi-asserted-by":"crossref","first-page":"6066","DOI":"10.1021\/ja01050a023","volume":"91","author":"Kluger R.","year":"1969","journal-title":"J. Am. Chem. Soc."},{"key":"ref19\/cit19c","doi-asserted-by":"crossref","first-page":"6006","DOI":"10.1021\/ja00307a027","volume":"107","author":"Kluger R.","year":"1985","journal-title":"J. Am. Chem. Soc."},{"key":"ref19\/cit19d","doi-asserted-by":"crossref","first-page":"207","DOI":"10.1021\/jo00352a014","volume":"51","author":"Kluger R.","year":"1986","journal-title":"J. Org. Chem."},{"key":"ref19\/cit19e","doi-asserted-by":"crossref","first-page":"109","DOI":"10.1021\/ar970154s","volume":"32","author":"Yang Y.-C.","year":"1999","journal-title":"Acc. Chem. Res."},{"key":"ref20\/cit20","doi-asserted-by":"crossref","first-page":"257","DOI":"10.1021\/ar50032a002","volume":"3","author":"Bunton C. A.","year":"1970","journal-title":"Acc. Chem. Res."},{"key":"ref21\/cit21","volume-title":"Gaussian 03","author":"Frisch M. J.","year":"2004"},{"key":"ref22\/cit22a","doi-asserted-by":"crossref","first-page":"327","DOI":"10.1016\/0009-2614(96)00349-1","volume":"255","author":"Cossi M.","year":"1996","journal-title":"Chem. Phys. Lett."},{"key":"ref22\/cit22b","doi-asserted-by":"crossref","first-page":"3032","DOI":"10.1063\/1.474659","volume":"107","author":"Cances E.","year":"1997","journal-title":"J. Chem. Phys."},{"key":"ref23\/cit23a","doi-asserted-by":"crossref","first-page":"8634","DOI":"10.1021\/jo049539w","volume":"69","author":"Vemula P. K.","year":"2004","journal-title":"J. Org. Chem."},{"key":"ref23\/cit23b","doi-asserted-by":"crossref","first-page":"9677","DOI":"10.1021\/jo050775w","volume":"70","author":"Bhattacharya S.","year":"2005","journal-title":"J. Org. Chem."},{"key":"ref24\/cit24","doi-asserted-by":"crossref","first-page":"2670","DOI":"10.1039\/jr9610002670","author":"Barnard P. W. C.","year":"1961","journal-title":"J. Chem. Soc."},{"key":"ref25\/cit25","doi-asserted-by":"crossref","first-page":"2154","DOI":"10.1063\/1.456010","volume":"90","author":"Gonzalez C.","year":"1989","journal-title":"J. Chem. 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