Photoinduced nucleophilic substitution of iodocubanes with arylthiolate and diphenylphosphanide ions. Experimental and computational approachesElectronic supplementary information (ESI) available: 1H NMR and 13C NMR spectra of new compounds, characterization data for known compounds, and computational information. See DOI: 10.1039/c8ra06275g

A new synthetic route to modify the cubane nucleus is reported here. Methyl-4-iodocubane-1-carboxylate ( 1 ) and 1,4-diiodocubane ( 2 ) were employed as reagents to react with arylthiolate and diphenylphosphanide ions under irradiation in liquid ammonia and dimethylsulphoxide. The reactions proceed...

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Bibliographic Details
Main Authors Jimenez, Liliana B, Puiatti, Marcelo, Andrada, Diego M, Brigante, Federico, Crespo Andrada, Karina F, Rossi, Roberto A, Priefer, Ronny, Pierini, Adriana B
Format Journal Article
LanguageEnglish
Published 23.11.2018
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Summary:A new synthetic route to modify the cubane nucleus is reported here. Methyl-4-iodocubane-1-carboxylate ( 1 ) and 1,4-diiodocubane ( 2 ) were employed as reagents to react with arylthiolate and diphenylphosphanide ions under irradiation in liquid ammonia and dimethylsulphoxide. The reactions proceed to afford thioaryl- and diphenylphosphoryl- cubane derivatives in moderate to good yields. It is also found that the monosubstituted product with retention of the second iodine is an intermediate compound. Mechanistic aspects are supported by DFT calculations. Photoinduced substitution of the cubane nucleus is reported here.
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H NMR and
13
C NMR spectra of new compounds, characterization data for known compounds, and computational information. See DOI
Electronic supplementary information (ESI) available
10.1039/c8ra06275g
ISSN:2046-2069
DOI:10.1039/c8ra06275g