2434-86-8

Usage

Uses

Used in Organic Synthesis:
(2R,3S)-bicyclo[2.2.1]hept-5-ene-2,3-diyldimethanediyl dimethanesulfonate is used as a reagent in organic synthesis for its ability to facilitate the formation of carbon-carbon bonds. Its unique bicyclic structure and sulfonate group make it a valuable component in creating complex organic molecules.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, (2R,3S)-bicyclo[2.2.1]hept-5-ene-2,3-diyldimethanediyl dimethanesulfonate is used as a building block for the synthesis of various pharmaceuticals. Its versatility allows it to be incorporated into the development of new drugs and medicinal compounds, contributing to advancements in healthcare and medicine.
Used in Chemical Reactions:
(2R,3S)-bicyclo[2.2.1]hept-5-ene-2,3-diyldimethanediyl dimethanesulfonate is utilized as a catalyst or intermediate in various chemical reactions. Its presence can enhance reaction rates, selectivity, or yield, making it an important tool in the field of chemistry for improving existing processes or enabling new ones.

Upstream product

• 129-64-6 bicyclo<2.2.1>-5-hepten-2endo,3endo-dicarboxylic anhydride 
• 124-63-0 methanesulfonyl chloride 
• 941567-71-1 (1R,2S,3R,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dimethanol 
• 542-92-7 cyclopenta-1,3-diene 
• 85-39-2 trans-5-norbornene-2,3-dimethanol 
• 129-64-6 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 

Downstream Products

• 88920-62-1 1-((1R,3S,7S)-4,4-Dioxo-4λ⁶-thia-tricyclo[5.2.1.0^2,6]dec-8-en-3-yl)-cyclohexanol 
• 83947-07-3 endo-4-thiatricyclo<5.2.1.0^2,6>dec-8-ene 4,4-dioxide 
• 95722-43-3 exo-9-oxa-endo-4-thiatricyclo<5.2.1.0^2,6>decane-4,4-dioxide 
• 53292-00-5 (1S,7R)-4-Thia-tricyclo[5.2.1.0^2,6]dec-8-ene 4,4-dioxide 

Relevant academic research and scientific papers

Removal of Nerve Agent Simulants from Water Using Light-Responsive Molecular Baskets

We found that molecular baskets 1-3, with amino acids at their rim, undergo photoinduced decarboxylations to give baskets 4-6 forming a solid precipitate in water. Furthermore, organophosphonates 7-9 (OP), akin in size and shape to G-type nerve agents, form inclusion complexes with baskets 1-3 (K = 6-2243 M-1). Light irradiation (300 nm) of an aqueous solution of 1-3?OP led to the formation of precipitate containing an OP compound thereby amounting to a novel strategy for light-induced sequestration of nerve agents or, perhaps, other targeted compounds. Importantly, the stability of basket OP complexes in addition to functional groups at the basket's rim play a role in the efficiency (up to 98%) by which OPs are removed from water.

Design and synthesis of polycyclic sulfones via Diels-Alder reaction and ring-rearrangement metathesis as key steps

Here, we describe a new and simple synthetic strategy to various polycyclic sulfones via Diels-Alder reaction and ring-rearrangement metathesis (RRM) as the key steps. This approach delivers tri- and tetracyclic sulfones with six (n = 1), seven (n = 2) or eight-membered (n = 3) fused-ring systems containing trans-ring junctions unlike the conventional all cis-ring junctions generally obtained during the RRM sequence. Interestingly the starting materials used are simple and commercially available.

Oligomeric benzylsulfonium salts: Facile benzylation via high-load ROMP reagents

(Chemical Equation Presented) The development of high-load, oligomeric benzylsulfonium salts, generated via ring-opening metathesis polymerization, and their utility in facile benzylations of various nucleophiles is reported. These oligomeric sulfonium salts exist as free-flowing powders and are stable at room temperature. After the benzylation event, purification is attained via simple dry load/filtration, followed by solvent removal to deliver products in excellent yield and purity.

A HIGHLY STEREOSELECTIVE SYNTHESIS OF (E)-1- SUBSTITUTED-1,3-DIENES.

(E)-1-substituted-1,3-dienes are obtained with high selectivity by the thermal extrusion of SO2 from 2-substituted-2,5-dihidrothiophene-1,1-dioxides generated by a retro Diels-Alder reaction.An application to the synthesis of (E)-9,11-dodecadien-1-yl acetate, a sex pheromone of the red-bollworm moth is described.

Degenerate Thermal Rearrangement of 1,3-Dimethylenecyclopentane. Evidence for Partially Stereospecific Biradical Formation and Closure in 1,3 Shift

Parolysis of 1,3-bis(dideuteriomethylene)cyclopentane at 370 deg C resulted in a first-order degenerate rearrangement in which the 1,3- and 3,3-shift products were formed in a 2:1 ratio, respectively, indicating the intermediacy of an effectively orthogonal 2,2'-bis(allylmethane) biradical.Pyrolysis of trans- and cis-4,5-dimethyl-1,3-dimethylenecyclopentane (T and C) gave 1,3- and 3,3-shift products with stereochemistry consistent with predominant conrotatory-bevel ring opening to produce the orthogonal diradical directly.Pyrolysis of optically active T gave the 1,3-shift products with 20.8percent inversion of configuration of the migrating carbon indicative of partial stereospecific closure of the biradical.Comparative pyrolysis of optically active T and its bis(dideuteriomethylene) derivative revealed no secondary kinetic deuterium isotop effect, but an alternation in the extent of racemization of starting material and amounts of 1,3- and 3,3-shift products indicates a product-determining isotope effect.These data provide further evidence for an intermediate.