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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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Supplementary files

Article information


Submitted
24 Jul 2018
Accepted
16 Nov 2018
First published
23 Nov 2018

This article is Open Access

RSC Adv., 2018,8, 39222-39230
Article type
Paper

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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