35544-39-9

Usage

Derivative of adamantane

A diamondoid hydrocarbon The compound is derived from adamantane, which is a hydrocarbon with a diamond-like structure.

Cyclic ether

A compound containing a ring of atoms with oxygen atoms 2,2'-Epidioxy-2,2'-biadamantane is a cyclic ether due to its structure containing ether groups in a cyclic form.

Two epoxide functional groups

Reactive chemical groups containing three-membered rings including an oxygen atom The compound has two epoxide groups, which contribute to its reactivity and make it useful in polymer synthesis.

Monomer in polymer synthesis

Building block for various polymers and copolymers 2,2'-Epidioxy-2,2'-biadamantane is commonly used as a monomer in the production of different polymers and copolymers.

Potential applications

Materials science, pharmaceuticals, and nanotechnology Due to its symmetrical and rigid molecular structure, EDBA has potential uses in various fields, including materials science, pharmaceuticals, and nanotechnology.

Drug delivery vehicle

A potential carrier for pharmaceutical compounds 2,2'-Epidioxy-2,2'-biadamantane is being researched for its potential as a drug delivery vehicle.

Building block for novel materials

A component for creating new materials with specific properties The compound can be used as a building block for developing new materials with tailored properties.

Toxicity

Can be toxic and harmful if not properly managed It is essential to handle 2,2'-Epidioxy-2,2'-biadamantane with care due to its potential toxicity and harmful effects.

Upstream product

• 30541-56-1 adamantylidene-adamantane 

Downstream Products

• 700-58-3 2-Adamantanone 
• 29186-07-0 bisadamantylidene epoxide 
• 29798-94-5 spiro[adamantane-2,2'-[2a]homoadamantan]-2'a-one 

Relevant academic research and scientific papers

Triphenylpyrylium Salt as Sensitizer for Electron Transfer Oxygenation not involving Superoxide Anion

2,4,6-Triphenylpyrylium tetrafluoroborate sensitized electron transfer oxygenation of adamantylideneadamantane proceeds via the reaction of the alkene radical cations with molecular oxygen without participation of superoxide anion.

Synthesis, characterization, photophysics and photochemistry of pyrylogen electron transfer sensitizers

A series of new dicationic sensitizers that are hybrids of pyrylium salts and viologens has been synthesized. The electrochemical and photophysical properties of these "pyrylogen" sensitizers are reported in sufficient detail to allow rationale design of new photoinduced electron transfer reactions. The range of their reduction potentials (+0.37-+0.05 V vs SCE) coupled with their range of singlet (48-63 kcal mol-1) and triplet (48-57 kcal mol-1) energies demonstrate that they are potent oxidizing agents in both their singlet and triplet excited states, thermodynamically capable of oxidizing substrates with oxidation potentials as high as 3.1 eV. The pyrylogens are synthesized in three steps from readily available starting materials in modest overall 11.4-22.3% yields. These sensitizers have the added advantages that: (1) their radical cations do not react on the CV timescale with oxygen bypassing the need to run reactions under nitrogen or argon and (2) have long wavelength absorptions between 413 and 523 nm well out of the range where competitive absorbance by most substrates would cause a problem. These new sensitizers do react with water requiring special precautions to operate in a dry reaction environment. Hybrids of pyrylium salts and viologens photochemically generate radical-cation/radical-cation pairs with substantial intra-ion repulsion that increases the rate constant of separation, kSEP, and competitively inhibits energy wasting return electron transfer. These first representatives of dicationic charge-shift sensitizers generate radical cations that do not react with oxygen on the CV timescale and absorb between 413 and 523 nm well outside the range where competitive absorbance by most substrates would cause a problem.

THE REACTION OF ADAMANTYLIDENEADAMANTANE WITH SINGLET OXYGEN MEDIATED BY ROSE BENGAL AND CHARGE TRANSFER COMPLEXES

Chemically generated singlet oxygen reacts with adamantylideneadamantane (1) in acetone solution to give mainly the corresponding 1,2-dioxetane (2) together with traces of the epoxide 3.When rose bengal (RB) is added to the reaction mixture, epoxide 3 becomes the chief product at the expense of the dioxetane 2, even in the dark.Charge transfer complexes (CTCs) formed between N-ethylcarbazole and fluorene with 2,4,7-trinitrofluoren-9-one and pyromellitic dianhydride, as well as quinhydrone, behave like RB in that their addition to the reaction mixture favors epoxide formation.Their epoxidizing power is related to the energies of their CT bands.Free energies (ΔG) calculated for the interaction of the CTC with singlet oxygen ranged from -2.07 to 0.45 kcal/mol.CTCs having a ΔG greater than 0.5 kcal/mol are inefficient for the production of 3.The results are explained in terms of two different processes.The normal course is the reaction of singlet oxygen with 1 to give dioxetane.Addends such as CTCs and dimeric RB compete for singlet oxygen and convert it to superoxide radical ion, which in a secondary process is indirectly responsible for epoxidation.

AUTOXIDATION OF ADAMANTYLIDENEADAMANTANE IN A PROTIC SOLVENT. FACILE PROTON-INDUCED ELECTRON TRANSFER FROM THE OLEFIN TO OXYGEN

Addition of trifluoroacetic acid to adamantylideneadamantane in dichloromethane solution under oxygen in the dark results in a rapid oxygenation of the olefin.The reaction is proposed to proceed through a mechanism involving proton-induced electon transfer from the olefin to oxygen giving its radical cation and a hydroperoxy radical followed by their subsequent reactions.