The Photostimulated Reaction of 1-Iodoadamantane with Carbanionic Nucleophiles in DMSO by the SRN1 Mechanism

Article abstract of DOI:10.1021/jo00299a001

1-Iodoadamantane (1) reacts under irradiation with the enolate ions of acetone (2), acetophenone (5a), and propiophenone (5b) to give adamantane and the substitution products in variable yields.The anion of nitromethane (7) does not react under irradiation with 1, but excellent yields of 1-adamantylnitromethane (8) are obtained in the photostimulated reaction of 1 and 7 in the presence of 2 or 5a (entrainment reactions).We suggest that 1-iodoadamantane reacts with these nucleophiles by the S_RN1 mechanism of nucleophilic substitution.