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Soc."},{"key":"ref13\/cit13","doi-asserted-by":"crossref","first-page":"3072","DOI":"10.1021\/jo01331a023","volume":"44","author":"Tomioka H.","year":"1979","journal-title":"J. Org. Chem."},{"key":"ref14\/cit14","doi-asserted-by":"crossref","first-page":"950","DOI":"10.1021\/ja00957a017","volume":"88","author":"Kaplan F.","year":"1966","journal-title":"J. Am. Chem. Soc."},{"key":"ref15\/cit15","doi-asserted-by":"crossref","first-page":"233","DOI":"10.1016\/S0040-4039(00)81373-8","volume":"24","author":"Wydila J.","year":"1983","journal-title":"Tetrahedron Lett."},{"key":"ref16\/cit16","first-page":"1261","volume":"91","author":"DoMinh T.","year":"1969","journal-title":"J. Am. Chem. Soc."},{"key":"ref17\/cit17","doi-asserted-by":"crossref","first-page":"5489","DOI":"10.1021\/jo060397a","volume":"71","author":"Candeias N. R.","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref18\/cit18","doi-asserted-by":"crossref","first-page":"6177","DOI":"10.1021\/cr030451c","volume":"104","author":"Moonen K.","year":"2004","journal-title":"Chem. Rev."},{"key":"ref19\/cit19","doi-asserted-by":"crossref","first-page":"863","DOI":"10.1021\/cr00094a007","volume":"89","author":"Maryanoff B. E.","year":"1989","journal-title":"Chem. Rev."},{"key":"ref20\/cit20","doi-asserted-by":"crossref","first-page":"3798","DOI":"10.1002\/ejoc.200300330","author":"Gois P. M. P.","year":"2003","journal-title":"Eur. J. Org. Chem."},{"key":"ref21\/cit21","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1016\/j.molcata.2004.09.041","volume":"227","author":"Gois P. M. P.","year":"2005","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref22\/cit22","doi-asserted-by":"crossref","first-page":"6571","DOI":"10.1016\/S0040-4039(03)01700-3","volume":"44","author":"Gois P. M. 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Rev."},{"key":"ref42\/cit42","unstructured":"Considering continuing assumption by the organic chemistry community on the reactivity of diazo substrates via singlet or triplet carbene species, it could be supposed for this case that it may occur via singlet carbene.(47-49)In line with this assumption, we performed DFT calculations assuming singlet carbene (derived from16a) as the reactive species, and the observed modeling reaction pathways were consistent with the experimental16b\/16cratio (Table4). However, due to recent studies by femtosecond flash photolysis which imply the formation of excited diazo species on the Wolff rearrangement(50)and 1,2-H shift,(51)another open possibility is that the C\u2212H insertion may occur instead via excited diazo species."},{"key":"ref43\/cit43","doi-asserted-by":"crossref","first-page":"1081","DOI":"10.1021\/ol050003m","volume":"7","author":"Choi M. K. W.","year":"2005","journal-title":"Org. 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