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

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 a...

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Autores principales: Jimenez, Liliana B., Puiatti, Marcelo, Andrada, Diego M., Brigante, Federico, Crespo Andrada, Karina F., Rossi, Roberto A., Priefer, Ronny, Pierini, Adriana B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9090936/
https://www.ncbi.nlm.nih.gov/pubmed/35558007
http://dx.doi.org/10.1039/c8ra06275g
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author Jimenez, Liliana B.
Puiatti, Marcelo
Andrada, Diego M.
Brigante, Federico
Crespo Andrada, Karina F.
Rossi, Roberto A.
Priefer, Ronny
Pierini, Adriana B.
author_facet Jimenez, Liliana B.
Puiatti, Marcelo
Andrada, Diego M.
Brigante, Federico
Crespo Andrada, Karina F.
Rossi, Roberto A.
Priefer, Ronny
Pierini, Adriana B.
author_sort Jimenez, Liliana B.
collection PubMed
description 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.
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spelling pubmed-90909362022-05-11 Photoinduced nucleophilic substitution of iodocubanes with arylthiolate and diphenylphosphanide ions. Experimental and computational approaches Jimenez, Liliana B. Puiatti, Marcelo Andrada, Diego M. Brigante, Federico Crespo Andrada, Karina F. Rossi, Roberto A. Priefer, Ronny Pierini, Adriana B. RSC Adv Chemistry 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. The Royal Society of Chemistry 2018-11-23 /pmc/articles/PMC9090936/ /pubmed/35558007 http://dx.doi.org/10.1039/c8ra06275g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Jimenez, Liliana B.
Puiatti, Marcelo
Andrada, Diego M.
Brigante, Federico
Crespo Andrada, Karina F.
Rossi, Roberto A.
Priefer, Ronny
Pierini, Adriana B.
Photoinduced nucleophilic substitution of iodocubanes with arylthiolate and diphenylphosphanide ions. Experimental and computational approaches
title Photoinduced nucleophilic substitution of iodocubanes with arylthiolate and diphenylphosphanide ions. Experimental and computational approaches
title_full Photoinduced nucleophilic substitution of iodocubanes with arylthiolate and diphenylphosphanide ions. Experimental and computational approaches
title_fullStr Photoinduced nucleophilic substitution of iodocubanes with arylthiolate and diphenylphosphanide ions. Experimental and computational approaches
title_full_unstemmed Photoinduced nucleophilic substitution of iodocubanes with arylthiolate and diphenylphosphanide ions. Experimental and computational approaches
title_short Photoinduced nucleophilic substitution of iodocubanes with arylthiolate and diphenylphosphanide ions. Experimental and computational approaches
title_sort photoinduced nucleophilic substitution of iodocubanes with arylthiolate and diphenylphosphanide ions. experimental and computational approaches
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9090936/
https://www.ncbi.nlm.nih.gov/pubmed/35558007
http://dx.doi.org/10.1039/c8ra06275g
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