52917-72-3

Basic information

• Product Name: ADAMANTANACETAMIDE
• Synonyms: ADAMANTANACETAMIDE
• CAS NO: 52917-72-3
• Molecular Formula: C₁₂H₁₉NO
• Molecular Weight: 193.29
• Mol File: 52917-72-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ADAMANTANACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ADAMANTANACETAMIDE(52917-72-3)
• EPA Substance Registry System: ADAMANTANACETAMIDE(52917-72-3)

Safety Data

• Hazardous Substances Data: 52917-72-3(Hazardous Substances Data)

Upstream product

• 281-23-2 adamantane 
• 75-05-8 acetonitrile 
• 118-75-2 chloranil 
• 196403-36-8 N-nitroso-N-(2-adamantyl)-O-benzylhydroxylamine 

Relevant articles and documents

The photochemical approach to the functionalization of open-chain and cyclic alkanes: 2. Hydrogen abstraction

Chloranil (Chl) has been irradiated in the presence of the alkanes 2,3-dimethylbutane, cyclohexane, norbornane, adamantane in acetonitrile. The primary step is hydrogen abstraction by triplet Chl, k(H) 0.8 to 2 x 106 M-1s-1, as confirmed by the detection of the ChlH. radical. Hydrogen abstraction from the alkanes is unselective. The thus formed alkyl radicals undergo different reaction, viz: coupling with ChlH· (both C-O coupling to give hydroquinonemonoethers and C-C coupling to give hydroxydihydrobenzofurans are observed); addition to ground state Chl to yield ultimately alkoxyphenoxyquinones; oxidation by groud state Chl (this process is fast only with tertiary radicals, and the cations formed in this case are trapped by the solvent MeCN to yield acetamides). Different methods for alkane functionalization are compared.

Oxidative functionalization of adamantane and some of its derivatives in solution

1,2,4,5-Benzenetetracarbonitrile (TCB) is irradiated in the presence of adamantane (1) and some of its derivatives. The singlet excited state of TCB is a strong oxidant, and there is various evidence, including time-resolved spectroscopy, to prove that SET from the alkane to TCB1* takes place and yields the corresponding radical ions. The adamantane radical cation deprotonates from the bridgehead position, and the resulting radical couples with TCB-*. Deprotonation via the radical cation occurs with a number of substituted adamantanes and remains the exclusive or predominating reaction also with derivatives containing a potential electrofugal group, such as one of the following carbocations: t-Bu, CH2OMe, CH2OH (notable here is that C-H deprotonation is more efficient than O-H deprotonation). A carboxy group is lost more efficiently than a proton, however. In contrast, detaching of such cations is the main process when the radical cations of substituted adamantanes is produced anodically. This different behavior is explained on the basis of thermochemical calculation and of the different environments experienced by the radical cation in the two cases, viz reaction from the solvated radical cation in the first case and from the substrate adsorbed on the anode in the latter one. 1-Methoxyadamantane deprotonates from the methyl group, a reaction explained by the different structure of the radical cation. On the other hand, the radical NO3*, conveniently produced by photolysis of cerium(IV) ammonium nitrate, reacts by hydrogen abstraction with selective attack at the bridgehead position and little interference by substituents and thus offers a useful way for the selective oxidative functionalization of adamantanes.

PHOTOCHEMICAL OXIDATION AND AUTOXIDATION OF SOME CYCLOALKANES PROMOTED BY CERIC AMMONIUM NITRATE IN ACETONITRILE

The oxidation and autoxidation of adamantane, norbornane and cyclohexane can be photochemically promoted by ceric ammonium nitrate in acetonitrile at room temperature, both processes being extremely efficient and selective with adamantane.