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Issue 69, 2018, Issue in Progress
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Photoinduced nucleophilic substitution of iodocubanes with arylthiolate and diphenylphosphanide ions. Experimental and computational approaches

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Abstract

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.

Graphical abstract: Photoinduced nucleophilic substitution of iodocubanes with arylthiolate and diphenylphosphanide ions. Experimental and computational approaches

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Publication details

The article was received on 24 Jul 2018, accepted on 16 Nov 2018 and first published on 23 Nov 2018


Article type: Paper
DOI: 10.1039/C8RA06275G
RSC Adv., 2018,8, 39222-39230
  • Open access: Creative Commons BY license
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    Photoinduced nucleophilic substitution of iodocubanes with arylthiolate and diphenylphosphanide ions. Experimental and computational approaches

    L. B. Jimenez, M. Puiatti, D. M. Andrada, F. Brigante, K. F. Crespo Andrada, R. A. Rossi, R. Priefer and A. B. Pierini, RSC Adv., 2018, 8, 39222
    DOI: 10.1039/C8RA06275G

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