1687-36-1

Usage

Uses

Used in Chemical Research:
1,3,5,7-Tetrmethyl-adamantane is used as a research compound for its distinctive molecular structure, which provides insights into the properties and behavior of alkyl-substituted adamantanes. Its highly symmetrical cage-like structure offers a unique platform for studying the effects of alkyl substitution on the physical and chemical characteristics of adamantane derivatives.
Used in Organic Chemistry:
1,3,5,7-Tetrmethyl-adamantane is used as a reference material in organic chemistry, allowing researchers to compare its properties with other hydrocarbons and understand the influence of the methyl groups on the overall chemical behavior of the molecule.
Used in Material Science:
1,3,5,7-Tetrmethyl-adamantane is used as a component in the development of new materials, leveraging its unique structural properties to create novel compounds with potential applications in various industries, such as pharmaceuticals, plastics, and coatings.
Used in Pharmaceutical Development:
1,3,5,7-Tetrmethyl-adamantane is used as a starting material or intermediate in the synthesis of complex organic molecules, including potential drug candidates, due to its unique structural features and reactivity.

InChI:InChI=1/C14H24/c1-11-5-12(2)8-13(3,6-11)10-14(4,7-11)9-12/h5-10H2,1-4H3

Upstream product

• 13755-04-9 <4,4,4>propellane 
• 768-90-1 1-Adamantyl bromide 
• 75-76-3 tetramethylsilane 
• 935-56-8 1-chloroadamantane 
• 281-23-2 adamantane 
• 768-95-6 1-adamanthanol 
• 53398-55-3 1-bromo-3,5,7-trimethyladamantane 
• 1678-91-7 ethyl-cyclohexane 
• 696-29-7 (1-methylethyl)-cyclohexane 
• 1678-98-4 isobutylcyclohexane 
• 75-16-1 methylmagnesium bromide 
• 82166-21-0 methyl cyclohexane 
• 74-88-4 methyl iodide 
• 41031-34-9 α-(1-adamantyl)cyclohexanone 

Relevant academic research and scientific papers

Exhaustive One-Step Bridgehead Methylation of Adamantane Derivatives with Tetramethylsilane

A methylation protocol of adamantane derivatives was investigated and optimized using AlCl3 and tetramethylsilane as the methylation agent. Substrates underwent exhaustive methylation of all available bridgehead positions with yields ranging from 62 to 86 %, and up to six methyl groups introduced in one step. Scaling-up of the reaction was demonstrated by performing the >40 gram-scale synthesis of 1,3,5,7-tetramethyladamantane with 62 % yield. For several substrates, rearrangements were observed, as well as cleavage of functional groups or Csp3?Csp2 bonds or even cyclohexyl-adamantyl bonds. Based on mechanistic studies, it is suggested that a reactive methylation complex is formed from tetramethylsilane and AlCl3. X-ray diffraction structures of hexamethylated bis-adamantyls reveal elongation or widening of sp3 carbon bonds between adamantyl moieties to 1.585(3) ? and 125.26(9)° due to repulsive H???H contacts.

Reaction of 1,3,5,7-Tetramethyladamantane with Nitric Acid

Abstract: The reaction of 1,3,5,7-tetramethyladamantane with fuming nitric acid leads to a mixture of 1,3,5,7-tetramethyladamantane-2,6-dione and syn/anti-6-nitroxy-1,3,5,7-tetramethyladamantan-2-one. 1,3,5,7-Tetramethyladamantane has an abnormally low reactivity due to the presence of methyl groups in the bridgehead positions of the cage.

Contribution a l'etude des reactions d'alkylation et de polyalkylation de l'adamantane et de ses homologues

A method for preparing alkyl derivatives of cage-structure compounds is proposed.It relies on the use of Grignard reactions with a high boiling point solvent.The reactions take place at atmospheric pressure.Methylation of adamantane, diamantane, and homoadamantane occurs with quantitative yield.With other primary alkyl groups, yields are better than 60percent.Competition between alkylation and secondary reactions is discussed on the basis of a free radical mechanism.

ADAMANTANE AND ITS DERIVATIVES IN IONIC METHYLATION

The ionic methylation of adamantane and 1-hydroxy-, 1-chloro-, and 1-bromoadamantanes was realized with tetramethylsilane in the presence of aluminum halides; the products were mono- and polyalkyladamantanes.Compounds of the adamantane series are methylated more readily than the analogous derivatives of cyclic and acyclic hydrocarbons of other types; the reaction takes place under mild conditions and leads to the production of methylation products with overall yields close to quantitative.