113975-50-1

Usage

Uses

Used in Organic Synthesis:
Cyclopropane, 1-ethenyl-2-ethoxy-, is used as a versatile building block in organic synthesis for the creation of various complex organic molecules. Its unique cyclopropane ring and functional groups allow for a wide range of chemical reactions, enabling the synthesis of diverse compounds with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Cyclopropane, 1-ethenyl-2-ethoxy-, is used as a key intermediate in the synthesis of various drugs and drug candidates. Its unique structure and reactivity make it a valuable component in the development of new medications with improved efficacy and selectivity.
Used in Agrochemical Industry:
Cyclopropane, 1-ethenyl-2-ethoxy-, is also utilized in the agrochemical industry as a building block for the synthesis of various agrochemicals, such as pesticides and herbicides. Its unique properties allow for the development of novel compounds with enhanced performance and selectivity in agricultural applications.
Used in Materials Science:
In the field of materials science, Cyclopropane, 1-ethenyl-2-ethoxy-, has potential applications in the development of new materials with unique properties. Its cyclopropane ring and functional groups can be incorporated into polymers, coatings, and other materials to impart specific characteristics, such as improved mechanical strength, thermal stability, or chemical resistance.
Used as a Reagent in Chemical Research:
Cyclopropane, 1-ethenyl-2-ethoxy-, is employed as a reagent in chemical research for the investigation of various chemical reactions and processes. Its unique structure and reactivity make it a valuable tool for studying reaction mechanisms, exploring new synthetic routes, and developing innovative methodologies in organic chemistry.

Upstream product

• 106-99-0 buta-1,3-diene 
• 3188-13-4 ethyl chloromethyl ether 
• 98065-89-5 (E/Z)-<1-(1',2',2'-trichlorovinyl)cyclopropyl> ethyl ether 
• 2032-04-4 vinyldiazomethane 
• 109-92-2 ethyl vinyl ether 
• 20834-16-6 (E)-(2-ethynylcyclopropyl) ethyl ether 

Downstream Products

• 113975-57-8 1,5-Bis(phenylthio)-1-ethoxypent-3-ene 
• 114030-39-6 (3aR,4R,6S,6aS)-4-Ethoxy-6-vinyl-tetrahydro-cyclopenta[1,3]dioxol-2-one 
• 114030-38-5 (3aR,4R,6R,6aS)-4-Ethoxy-6-vinyl-tetrahydro-cyclopenta[1,3]dioxol-2-one 
• 113975-54-5 (3aR,4S,6S,6aS)-4-Ethoxy-6-vinyl-tetrahydro-cyclopenta[1,3]dioxol-2-one 

Relevant academic research and scientific papers

On the substituent effects of the thermal ethenylcyclopropane-to-cyclopentene rearrangement: Gas-phase kinetics of ethoxy-, methylthio-and trimethylsilyl-substituted ethenylcyclopropanes

A series of 1- and 2-substituted ethenylcyclopropanes were prepared in high yields and subjected to gas-phase pyrolytic kinetic investigations. All ethenylcyclopropanes rearranged cleanly to the correspondingly substituted cyclopentenes, although in the case of the 2-substituted compounds, cis/trans isomerization was additionally observed (both stereoisomers were investigated in these cases). All rearrangements obeyed first-order kinetics independent of pressure and surface-to-volume ratio. Reasonable Arrhenius parameters were obtained for these homogeneous, unimolecular reactions. 1-Trimethylsilyl and 1-methylthio substituents produced modest rate accelerations, consistent with biradical mechanisms. A previous finding of rate retardation by 1-trimethylsilyl substitution is attributed to steric hindrance. 2-Ethoxy and 2-methylthio substituents [in both (E)- and (Z)-configurations] produced greater rate accelerations, inconsistent with biradical mechanisms. The steric effects on the kinetics of the (Z)-isomer rearrangements appear relatively unimportant. The methylthio substituent effects are documented and analyzed for the first time. Wiley-VCH Verlag GmbH, 2001.

Dirhodium(II) tetraacetate catalyzed (chlorovinyl)cyclopropanation of enol ethers and dienol ethers - A route to donor-substituted vinylcyclopropanes, ethynylcyclopropanes and cycloheptadienes

2-Chloro- (4-Cl), 3,3-dichloro- (4-Cl2), and 2,3,3-trichlorodiazo-propene (4-Cl3) can easily be prepared in up to 70% yield by thermal fragmentation (Bamford-Stevens reaction), at 60°C in tetrahydrofuran, of the corresponding chloroacrolein tosylhydrazone sodium salts 3-Cl(n). Tetrahydrofuran solutions of (chlorovinyl)diazomethanes 4-Cl(n) thus obtained are used for cyclopropanation reactions of a large variety of alkenes. Under dirhodium(II) tetraacetate catalysis, yields of (chlorovinyl)cyclopropanes 6-Cl(n) [and of vinylcyclopropanes 6-H3 with diazopropene (4-H3)] are quite good especially from enol ethers. Dienol silyl ethers, 2-trimethylsiloxy-1,3-butadiene (12) and 1-(1'-trimethyl-siloxyvinyl)cyclohexene (15), react exclusively at the donor-substituted double bond, the resulting 1-siloxy-1,2-divinylcyclopropanes 13-X(n), 16-X(n) readily rearrange to cycloheptadiene derivatives 14 and 17-20 respectively. 2-Alkoxy-1-(chlorovinyl)cyclopropanes such as 6 o-Cl2, 6 p-Cl2, 6 p-Cl3 can be transformed to synthetically valuable 2-alkoxy-1-ethynylcyclopropanes 27 o,p, which are also obtained by direct ethynylcyclopropanation of enol ethers with diazopropyne (28). This latter method provides the first known access to 2-siloxy-1-ethynylcyclopropane 25m.