840-90-4

Usage

Uses

Used in Organic Synthesis:
Bicyclo[2.2.1]hept-2-yl 4-methylbenzenesulfonate serves as a valuable intermediate in organic synthesis, leveraging its distinct molecular structure to facilitate the creation of complex organic molecules and contribute to the advancement of chemical research.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, bicyclo[2.2.1]hept-2-yl 4-methylbenzenesulfonate is utilized as a building block for the development of new drugs. Its unique structure allows it to be a key component in the synthesis of pharmaceutical compounds, potentially leading to innovative treatments and therapies.
Used as a Chemical Reactant:
Due to its reactivity, bicyclo[2.2.1]hept-2-yl 4-methylbenzenesulfonate can be employed in various chemical reactions, acting as a reactant to produce a range of different chemical products. This versatility makes it a useful tool in the field of chemistry for diverse applications.

Upstream product

• 23730-25-8 Bicyclo<3.1.1>hept-2-yl p-toluenesulfinate 
• 497-36-9 (+/-)-endo-2-norborneol 
• 98-59-9 p-toluenesulfonyl chloride 
• 497-37-0 (2R)-(+)-exo-2-norborneol 

Downstream Products

• 498-66-8 norbornene 
• 50414-49-8 2-exo-phenyloxybicyclo[2.2.1]heptane 
• 17152-43-1 o-Norborn-2-yl-phenol 
• 279-19-6 nortricyclane 
• 17152-77-1 p-Norborn-2-yl-phenol 
• 79602-21-4 2-(4-phenoxybutoxy)norbornane 
• 100871-13-4 (+/-)-3,5-dinitro-benzoic acid-[2exo]norbornyl ester 
• 61242-45-3 (+/-)-phthalic acid mono-[2exo]norbornyl ester 
• 61242-45-3 phthalic acid mono-((1R)-[2exo]norbornyl ester) 
• 34640-76-1 (+-)-2exo-acetoxy-norbornane 
• 61277-92-7 phthalic acid mono-((1S)-[2exo]norbornyl ester) 
• 497-37-0 (2R)-(+)-exo-2-norborneol 
• 497-36-9 (1S,2S,4R)-2-norbornanol 
• 497-38-1 (1S,4R)-bicyclo[2.2.1]heptan-2-one 

Relevant academic research and scientific papers

Cobalt-Catalyzed Silylcarbonylation of Unactivated Secondary Alkyl Tosylates at Low Pressure

A catalytic preparation of silyl enol ethers from unactivated secondary alkyl tosylates is reported. An inexpensive cobalt catalyst is used under mild conditions with low pressures of carbon monoxide. Nucleophilic, anionic cobalt carbonyls facilitate the catalytic activation of a range of alkyl tosylates. The silylcarbonylation offers a practical approach to synthetically valuable silyl enol ethers from simple starting materials.

Norpinyl-Norbornyl Rearrangements: Destabilized 2-Norpinyl Cations

In order to explore the effect of electron-withdrawing substituents on 2-norpinyl (bicyclohept-2-yl) -> 2-norbornyl (bicyclohept-2-yl) rearrangements, cyano and pentafluoroethyl groups were introduced into the α and β (= bridgehead) positions.The substrates were synthesized from norpinan-2-one (8) by addition of HCN or C2H5Li, from 2-aminonorbornane-2-carbonitrile (25) by rearrangement, and from 1-(pentafluoroethyl)bicyclohexan-2-one (51) by ring expansion.Arenesulfonates and diazonium ions were used to generate the 2-norpinyl cations. - Electron acceptors in the α position of 2-norpinyl substrates promote the norpinyl -> norbornyl rearrangement.Internal return of the counterion leads to endo-2-norbornyl sulfonates, often without formation of the analogous alcohols, i.e., the destabilized norpinyl cations do not escape from tight ion pairs.Electron acceptors in the β (bridgehead) position favor displacement and elimination processes with retention of the norpinyl structure while the norpinyl -> norbornyl rearrangement is inhibited, more strongly by β-C2F5 than by β-CN.The tendency to separate the positive charge from the electron acceptor explains the divergent effects of α and β substitution. - The kH/kα-CN and kH/kβ-CN rate ratios in the 2-norpinyl and 2-norbornyl series are virtually the same, and the stereoselectivity of the intervening carbocations is not significantly affected by electron-withdrawing substituents. - Keywords: 1,2-Alkyl shifts / Ring expansion / Destabilized carbocations / Stereoselectivity / ? Delocalization

Base-Promoted 1,2-Eliminations from endo-2-Bicycloheptyl Halides and Arenesulfonates

Base-solvent systems that provide clean bimolecular 1,2-elimination from endo-2-bicycloheptyl halides and arenesulfonates by suppressing competitive solvolysis and nortricyclene-forming 1,3-elimination are developed.The stereochemistries of elimination from exo-3-deuterio-endo-2-bromobicycloheptane (10) and exo-3-deuterio-endo-2-bicycloheptyl 2,4,6-triisopropylbenzenesulfonate (11) are assessed using these base-solvent systems.The competitive syn-endo and anti-exo-H elimination modes are found to be strongly influenced by base association.However, for dissociated alkoxide bases, the elimination stereochemistry is unaffected by changes in leaving group from halide to arenesulfonate, in base strength, and in base size.

Application of Mechanistic and Transition-State Indicators to endo and exo-2-Norbornyl Arenesulfonates. Definition of a new Mechanistic Indicator

We have mechanistically classified endo- and exo-2-norbornyl arenesulfonates by using two common probes: the effect on rate of added thiourea and rate correlation in aqueous ethanol and trifluoroethanol.Interestingly, the exo isomer is improperly classified by each of these probes because of medium-dependent ion-pair return.In search of better mechanistic indicators, pseudo-first-order solvolytic rates and products have been determined for a series of endo- and exo-2-norbornyl arenesulfonates.Using these and literature data, we have compared these substrates with others by plotting α-deuterium isotope effects against β1gMe values determined for a series or arenesulfonates in the same or a similar solvent.The use of this type of plot as a heuristic method for distinguishing k8 and kΔ substrates is discussed.Finally, our product studies are consistent with the involvement of solvent-seperated ion pairs in the solvolysis of 2-norbornyl arenesulfonates.Different alcohol-ether product ratios for the isomeric esters in consistent with dual pathways for product formation with the endo substrates.