768-93-4 Usage
Description
1-Iodoadamantane is a haloadamantane, a solid compound with unique chemical properties. It is known for its reactivity in various chemical reactions, making it a valuable compound for research and industrial applications.
Uses
Used in Chemical Research:
1-Iodoadamantane is used as a suitable reagent for evaluating the rate constants for the reduction of haloadamantanes by SmI2 in the presence of hexamethylphosphoramide (HMPA) and H2O. This is done through a GC/MS-analyzed method, which helps in understanding the reaction mechanisms and kinetics.
Used in Reactive Systems Investigation:
1-Iodoadamantane serves as an iodine atom donor for probing the intermediacy of radical reactions. It is particularly useful in investigating the chemistry of highly reactive, strained systems such as propellane.
Used in Synthesis of N-(1-Adamantyl)acetamide:
1-Iodoadamantane can be used as a starting reagent in the synthesis of N-(1-adamantyl)acetamide via nucleophilic substitution. 1-IODOADAMANTANE has potential applications in various fields, including pharmaceuticals and materials science.
Used in Free-Radical Carbonylation Reactions:
1-Iodoadamantane may be employed in free-radical carbonylation reactions with alkenes. These reactions can lead to the formation of various valuable products, contributing to the development of new synthetic routes and applications in the chemical industry.
Used in Photoinduced Reactions:
1-Iodoadamantane is involved in photoinduced reactions in DMSO, which afford substitution products on C3, C6, and C8, 1-adamantanol, 1-adamantyl 2-naphthyl ether, and adamantine. These reactions can provide insights into the reactivity and potential applications of 1-iodoadamantane in various chemical processes.
Used in Phthalimide Anion Reactions:
The photostimulated reaction of the phthalimide anion with 1-iodoadamantane yields 3-(1-adamantyl) phthalimide and 4-(1-adamantyl) phthalimide, along with the reduction product adamantane. This reaction demonstrates the versatility of 1-iodoadamantane in forming different products and its potential use in the synthesis of various compounds.
Used in Enolate Anion Reactions:
1-Iodoadamantane undergoes photostimulated reactions with the enolate anion of acetone, acetophenone, and propiophenone to give admantane and the substitution products. These reactions highlight the compound's reactivity and its potential use in the synthesis of various organic compounds.
Synthesis Reference(s)
The Journal of Organic Chemistry, 48, p. 2766, 1983 DOI: 10.1021/jo00164a026
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 768-93-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,6 and 8 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 768-93:
(5*7)+(4*6)+(3*8)+(2*9)+(1*3)=104
104 % 10 = 4
So 768-93-4 is a valid CAS Registry Number.
InChI:InChI=1/C10H15I/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6H2
768-93-4Relevant articles and documents
Selective C-F bond activation: Substitution of unactivated alkyl fluorides using YbI3
Traeff, Annika M.,Janjetovic, Mario,Ta, Linda,Hilmersson, Goeran
supporting information, p. 12073 - 12076 (2013/12/04)
F makes the break: The carbon-fluorine single bond is quite strong, thus making aliphatic C-F bond scission unusually challenging. A new methodology utilizing YbI3 leads to the conversion of a C-F bond into a C-I bond, and is compatible with various functional groups. The reaction is exceptionally selective towards alkyl fluorides and proceeds under mild conditions. Copyright
Mechanistic Definition of Trimethylstannylation of 1,3-Dihaloadamantanes: Delocalized Radical Anions as Possible Intermediates
Adcock, William,Clark, Christopher I.
, p. 7341 - 7349 (2007/10/02)
A series of 1,3-dihaloadamantanes (3, X = Y = halogens) have been synthesized, characterized, and treated with (trimethylstannyl) alkali reagents (Me3SnM, M = Li or Na) in the absence and presence of tert-butylamine (TBA) and dicyclohexylphosphine (DCPH).The product distributions of these reactions have been established by 13C and 119Sn NMR spectroscopy and vapour-phase chromatographic analyses.The substitution via an SRN1-type pathway is shown to be a significant reaction for several of the derivatives of 3 (X = F, Y = Br or I; X = Cl, Y = Br or I; X = Y = Br) but not for the bromo iodide or diiodide (3, X = Br, Y = I and X = Y =I).For the latter two compounds, the formation of 1,3-dehydroadamantane or propellane 8 is the predominant reaction product while tin substitution is insignificant.Propellane 8 formation is also a significant reaction product for some of the other dihalo derivatives of 3 (X = Cl, Y = I and X = Y = Br) but not for others (3, X = F, Y = Br or I and X = Cl, Y = Br).The mechanism of formation of 8 is perplexing in light of the trapping experiments in the presence of TBA and DCPH.A possible pathway is proposed in wich the key intermediate is a delocalized radical anion.
Decarboxylative Iodination: A Convenient Synthesis of Bridgehead Iodides
Abeywickrema, Ramyani S.,Della, Ernest W.
, p. 4226 - 4229 (2007/10/02)
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