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

PUIATTI, MARCELO

RSC Advances

Royal Chemical Society

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

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 thioarylanddiphenylphosphoryl- 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.