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Title

A theoretical and experimental study of the racemization process of hexaaza[5]helicenes

AuthorsAbarca, B.; Ballesteros, R.; Adam, Rosa; Ballesteros-Garrido, R.; Leroux, Frédérc R.; Colobert, François; Alkorta, Ibon ; Elguero, José
KeywordsDiazoimine–triazole equilibrium
Racemization barriers
Helical chirality
Azahelicenes
Issue Date2014
PublisherElsevier
CitationTetrahedron 70: 8750-8757 (2014)
AbstractA dynamic 1H NMR study, together with DFT calculations, of bis-([1,2,3]triazolo)[1,5-a:5′,1′-k][1,10]phenanthroline 2 has allowed to identify the ring and open forms of a new example of ring/chain tautomerism, as well as their interconversion barriers (ring/ring and ring/open). The barrier of the exchange process between the chain forms and the ring form was found higher than the 'racemization' process in the closed form, so the ring opening does not contribute to the 'racemization'. The di-1,10-methyl and di-1,10-iodo derivatives have been prepared and their properties calculated.
URIhttp://hdl.handle.net/10261/108016
DOI10.1016/j.tet.2014.09.018
Identifiersdoi: 10.1016/j.tet.2014.09.018
issn: 1464-5416
Appears in Collections:(IQM) Artículos
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