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

ANDRADA D.; ROSSI R.; JIMENEZ L.; BRIGANTE F.; JIMENEZ L.; PRIEFER R.; BRIGANTE F.; PRIEFER R.; PUIATTI M.; CRESPO ANDRADA K,; PIERINI A,; PUIATTI M.; CRESPO ANDRADA K,; PIERINI A,; ANDRADA D.; ROSSI R.

RCS Advances

Royal Society of Chemistry

Lugar: Londres; Año: 2018 vol. 8 p. 39222 - 39230

2046-2069

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 diphenylphosphanideions 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 themonosubstituted product with retention of the second iodine is an intermediate compound. Mechanisticaspects are supported by DFT calculations.