Description

• General description: 1-Iodoadamantane is a haloadamantane.[1] Voltammetric reduction of 1-iodoadamantane at a silver cathode in tetrahydrofuran (THF) and acetonitrile (ACN) is reported to involve a single electron forming a mixture of monomeric and dimeric products.[2] The photoinduced reaction of 1-iodoadamantane in DMSO is reported to afford substitution products on C3, C6, and C8, 1-adamantanol, 1-adamantyl 2-naphthyl ether, and adamantine.[3] The photostimulated reaction of the phthalimide anion with 1-iodoadamantane is reported to yield 3-(1-adamantyl) phthalimide and 4-(1-adamantyl) phthalimide, along with the reduction product adamantane.[4] 1-Iodoadamantane is reported to undergoe photostimulated reaction with the enolate anion of acetone, acetophenone and propiophenone to give admantane and the substitution products.[5]
• Application: 1-Iodoadamantane is suitable reagent used to evaluate the rate constants for the reduction of haloadamantanes by SmI2 in presence of hexamethylphosphoramide (HMPA) and H2O by GC/MS-analyzed method.[1] It may be used as iodine atom donor for probing the intermediacy of radical to investigate the chemistry of highly reactive, strained systems such as propellane.[6] It may be used as starting reagent in the synthesis of N-(1-adamantyl)acetamide via nucleophilic substitution.[7] It may be employed in the free-radical carbonylation reactions with alkenes.[8][9]