Chemical Properties
solid
Uses
1-Iodoadamantane is suitable reagent used to evaluate the rate constants for the reduction of haloadamantanes by SmI
2 in presence of hexamethylphosphoramide (HMPA) and H
2O by GC/MS-analyzed method. 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. It may be used as starting reagent in the synthesis of
N-(1-adamantyl)acetamide
via nucleophilic substitution. It may be employed in the free-radical carbonylation reactions with alkenes.
Synthesis Reference(s)
The Journal of Organic Chemistry, 48, p. 2766, 1983
DOI: 10.1021/jo00164a026
General Description
1-Iodoadamantane is a haloadamantane. 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. 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. 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. 1-Iodoadamantane is reported to undergoe photostimulated reaction with the enolate anion of acetone, acetophenone and propiophenone to give admantane and the substitution products.
Purification Methods
Dissolve the iodide in Et2O, shake with aqueous NaHSO3, aqueous K2CO3, and H2O, dry (Na2SO4), evaporate and recrystallise it from MeOH at -70o (to avoid alcoholysis) to give white crystals. [Schleyer & Nicholas J Am Chem Soc 83 2700 1961, lit m of 151-152.5o is incorrect.] Also purify by recrystallisation from pet ether (40-60oC) followed by rigorous drying and repeated sublimation. [Beilstein 5 IV 470.]
