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Soc."},{"key":"ref7\/cit7","doi-asserted-by":"crossref","first-page":"5787","DOI":"10.1021\/ja010234y","volume":"123","author":"Bach R. D.","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"ref8\/cit8","doi-asserted-by":"crossref","first-page":"1073","DOI":"10.1016\/S0040-4039(01)85455-1","author":"See Rappoport Z.","year":"1978","journal-title":"Tetrahedron Lett."},{"key":"ref9\/cit9a","doi-asserted-by":"crossref","first-page":"4527","DOI":"10.1021\/ja00064a014","volume":"115","author":"Luccini V.","year":"1993","journal-title":"J. Am. Chem. Soc."},{"key":"ref9\/cit9b","doi-asserted-by":"crossref","first-page":"2297","DOI":"10.1021\/ja00113a018","volume":"117","author":"Luccini V.","year":"1995","journal-title":"J. Am. Chem. Soc."},{"key":"ref10\/cit10","doi-asserted-by":"crossref","first-page":"6868","DOI":"10.1021\/ja0482684","volume":"126","author":"Shiers J. J.","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref11\/cit11","doi-asserted-by":"crossref","first-page":"2461","DOI":"10.1021\/ol049119t","volume":"6","author":"Ando K.","year":"2004","journal-title":"Org. Lett."},{"key":"ref12\/cit12","doi-asserted-by":"crossref","first-page":"4203","DOI":"10.1021\/jo035604a","volume":"69","author":"Ando K.","year":"2004","journal-title":"J. Org. Chem."},{"key":"ref13\/cit13","doi-asserted-by":"crossref","first-page":"3360","DOI":"10.1021\/ja00117a006","volume":"117","author":"Okuyama T.","year":"1995","journal-title":"J. Am. Chem. Soc."},{"key":"ref14\/cit14","doi-asserted-by":"crossref","first-page":"7059","DOI":"10.1021\/ja00018a066","volume":"113","author":"Ochiai M.","year":"1991","journal-title":"J. Am. Chem. Soc."},{"key":"ref15\/cit15","doi-asserted-by":"crossref","first-page":"2275","DOI":"10.1021\/ja972267c","volume":"120","author":"Okuyama T.","year":"1998","journal-title":"J. Am. Chem. 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Chem."},{"key":"ref31\/cit31","unstructured":"The intrinsic rate constant is the rate constant in the absence of thermodynamic driving force (\u0394G\u00b0 = 0) and is obtained from interpolation or extrapolation of logk1versus logK1toK1= 1."},{"key":"ref32\/cit32","unstructured":"MA = Meldrum\u2019s acid moiety; ID = 1,3-indandione moiety."},{"key":"ref33\/cit33a","doi-asserted-by":"crossref","first-page":"301","DOI":"10.1021\/ar00140a006","volume":"20","author":"Bernasconi C. F.","year":"1987","journal-title":"Acc. Chem. Res."},{"key":"ref33\/cit33b","first-page":"119","volume":"27","author":"Bernasconi C. F.","year":"1992","journal-title":"Adv. Phys. Org."},{"key":"ref34\/cit34","unstructured":"Late development in one direction equals early loss in the reverse direction.(33)."},{"key":"ref35\/cit35","doi-asserted-by":"crossref","first-page":"4937","DOI":"10.1021\/ja00013a033","volume":"113","author":"Bernasconi C. F.","year":"1991","journal-title":"J. Am. Chem. 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