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Usage

Uses

Used in Pharmaceutical Synthesis:
2-(bicyclo[2.2.1]hept-5-en-2-yl)oxirane is used as a reactant in the synthesis of various pharmaceuticals for its ability to form complex molecular structures. Its high reactivity allows for the creation of diverse chemical entities that can be utilized in medicinal chemistry.
Used in Polymer Production:
In the polymer industry, 2-(bicyclo[2.2.1]hept-5-en-2-yl)oxirane is used as a monomer in the production of different polymers and copolymers. It is particularly valuable in the creation of specialty plastics and adhesives, where its unique structural properties contribute to the desired material characteristics.
Used in Organic Synthesis:
2-(bicyclo[2.2.1]hept-5-en-2-yl)oxirane is utilized as a building block in organic synthesis for the construction of complex organic molecules. Its strained ring system facilitates unique reaction pathways, making it a useful component in the synthesis of a variety of organic compounds.
Safety Considerations:
Given its reactivity and potential hazards, appropriate safety precautions should be taken when handling 2-(bicyclo[2.2.1]hept-5-en-2-yl)oxirane. This includes the use of protective equipment and adherence to proper handling and storage protocols to minimize risks associated with its use in various applications.

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 3048-64-4 5-vinyl-2-norbornene 
• 5453-80-5 5-Norbornene-2-carboxaldehyde 
• 2181-42-2 trimethylsulphonium iodide 

Relevant academic research and scientific papers

Synthesis of a norbornene monomer having cyclic carbonate moiety based on CO2 fixation and its transition metal-catalyzed polymerizations

A norbornene monomer bearing cyclic carbonate moiety (NB-CC) was successfully synthesized from the corresponding precursor having epoxy moiety by its reaction with carbon dioxide under atmospheric pressure, which was efficiently catalyzed by lithium bromide. NB-CC underwent the ring-opening metathesis polymerization (ROMP) catalyzed by a ruthenium carbene complex to give the corresponding poly-(norbornene), of which side chain inherited the cyclic carbonate moiety from the monomer without any deterioration. The same ROMP system was applicable to the copolymerization of NB-CC and 5-butyl-2-norbornene (BNB), which afforded the corresponding copolymer with a composition ratio same as a feed ratio. In addition, by using a catalytic system consisted of palladium (II) acetate/tricyclohexylphosphine/triphenylcarbenium tetrakis(pentafluorophenyl)borate, the copolymerization of NB-CC and BNC proceeded successfully in a vinyl addition polymerization mode to give the corresponding poly(norbornene) having CC moiety in the side chain.

Synthesis of reactive poly(norbornene): Ring-opening metathesis polymerization of norbornene monomer bearing cyclic dithiocarbonate moiety

A norbornene monomer bearing cyclic dithiocarbonate moiety (NB-DTC) was successfully synthesized from the corresponding precursor having epoxy moiety by its reaction with carbon disulfide. NB-DTC underwent the ring-opening metathesis polymerization (ROMP) catalyzed by a ruthenium carbene complex to give the corresponding poly(norbornene). The dithiocarbonate moiety incorporated into the side chain of the obtained poly(norbornene) reacted with amine to afford the corresponding thiourethane moiety with thiol group, which underwent oxidative S-S coupling and/or addition reaction to the C-C double bond in the main chain, leading to formation of a cross-linked polymer.

Catalytic epoxidation of 5-vinyl-2-norbornene with organic hydroperoxides

5-Vinyl-2-norbornene is epoxidized with tert-butyl, tert-amyl, or cumyl hydroperoxide in the presence of molybdenyl ethanediolate at either of both of the double bonds of the hydrocarbon to afford preferentially 2,3-epoxy-5-vinylnorbornane. The reactivity of tert-alkyl hydroperoxides correlates with their structure characterized by the Taft polar substituent constants. The ρ* value found to be 1.08 confirms the electrophilic character of the catalytic hydroperoxide epoxidation and indicates a low polarity of the activated complex of the reaction.