2781-85-3

Usage

Uses

1. Used in Chemical Synthesis:
Cyclopropene is used as a building block for the synthesis of various organic compounds due to its unique ring structure and the presence of a double bond.
2. Used in Pharmaceutical Industry:
Cyclopropene is used as an intermediate in the development of pharmaceutical compounds, taking advantage of its reactive nature and potential for functional group transformations.
3. Used in Material Science:
Cyclopropene can be utilized in the creation of novel materials with specific properties, such as polymers with unique mechanical or electronic characteristics, by incorporating cyclopropene into their molecular structure.
4. Used in Agrochemicals:
Cyclopropene may be employed as a precursor in the development of agrochemicals, such as pesticides or herbicides, due to its potential for chemical modification and reactivity.
5. Used in Research and Development:
Cyclopropene serves as a valuable research tool for studying the properties and reactions of cycloalkenes, contributing to the advancement of organic chemistry and related fields.

Upstream product

• 110-00-9 furan 
• 19533-50-7 1,2-dibromo-cyclopropane 
• 107-05-1 3-chloroprop-1-ene 
• 1981-80-2 allyl radical 
• 31507-76-3 cyclopropyl-trimethyl-ammonium; hydroxide 
• 498-60-2 furan-3-carboxaldehyde 
• 159395-10-5 1-chloro-2-(trimethylsilyl)cyclopropane 
• 64-17-5 ethanol 
• 51525-97-4 1,1,3,3-tetrabromopropane 
• 82323-32-8 2-methylene-4-methyl-5,6-diphenyltetracyclo<5.4.0.0^1,5.0^4,6>undeca-8,10-diene 
• 4333-56-6 cyclopropyl bromide 
• 74-85-1 ethene 
• 75-25-2 Bromoform 

Downstream Products

• 51525-97-4 1,1,3,3-tetrabromopropane 
• 19533-50-7 1,2-dibromo-cyclopropane 
• 19533-52-9 1,2-diiodo-cyclopropane 
• 50915-85-0 C₁₀H₁₄ 
• 50915-91-8 1-Butyl-2-ethyl-cyclopropene 
• 50915-81-6 1-butylcyclopropene 
• 34189-00-9 1-Ethylcyclopropene 
• 34189-01-0 1,2-Diaethylcyclopropen 
• 50915-94-1 (2,2-Dimethoxy-ethylidene)-cyclopropane 
• 83747-32-4 2,5-Di-tert-butyl-cyclohepta-1,3,5-triene 
• 50915-84-9 1-(3,5,5-trimethylhexyl)-cyclopropene 
• 50915-86-1 1-Isobutyl-cyclopropene 
• 50915-82-7 1-hexylcyclopropene 
• 50915-83-8 1-octylcyclopropene 

Relevant academic research and scientific papers

Photodissociation dynamics of the allyl radical

The photochemistry and photodissociation dynamics of the allyl radical upon ultraviolet (UV) excitation is investigated in a molecular beam by using time- and frequency-resolved photoionization of hydrogen atoms with Lyman-a-radiation. The UV states of allyl decay by internal conversion to the ground state, forming vibrationally hot radicals that lose hydrogen atoms on a nanosecond time scale. Two channels are identified, formation of allene directly from allyl, and isomerization from allyl to 2-propenyl, with a subsequent hydrogen loss, resulting in both allene and propyne formation. The branching ratio is between 2:1 and 3:1, with direct formation of allene being the dominant reaction channel. This channel is associated with site-selective loss of hydrogen from the central carbon atom, as observed in experiments on isotopically labeled radicals. Ab initio calculations of the reaction pathways and Rice-Ramsperger-Kassel-Marcus (RRKM) calculations of the rates are in agreement with the mechanism and branching ratios. From the measured Doppler profiles a translational energy release of 14±1 kcal/mol is calculated. The calculated value of 66 kcal/mol for the barrier to the 1,2 hydrogen shift from allyl radical to 2-propenyl is confirmed by the experimental data.

Kinetics and dynamics in the photodissociation of the allyl radical

The direct observation of the products, kinetics and translational energy release from the photodissociation of the allyl radical, C3H5, upon excitation in the near-uv is reported. A statistical analysis of the data shows that they are in agreement with allene formation being the dominant H-loss reaction channel.

Photocycloadditions of tetrachloro-1,4-benzoquinone (chloranil) onto cyclobutene and cyclopropene. Expected and unexpected products

Solutions of chloranil (CA) in chlorobenzene were irradiated in the presence of cyclobutene and cyclopropene. Cyclobutene gave rise to two conventional 1:2 cycloadducts onto the dichloroethene subunits of CA and an α,β-unsaturated α,γ-dichloro-γ-lactone. Heating of the crude product in methanol converted the lactone into an α,β- unsaturated methyl γ-oxocarboxylate (25% yield) and a large amount of the major 1:2 cycloadduct, which contains chlorocyclobutane entities, into a cyclopropylcarbinyl chloride derivative (24% yield). An entirely new product type was the result in the case of cyclopropene. After treatment of the crude product with methanol a tetracyclic acetal containing a cyclopentanone and a dihydropyran subunit was isolated in 36% yield. Apparently, CA had taken up two molecules of cyclopropene. One of the resulting cyclopropane entities must have undergone a rearrangement en route to the final product.

Stereo- and Regioselective 1,3-Dipolar Cycloaddition of the Stable Ninhydrin-Derived Azomethine Ylide to Cyclopropenes: Trapping of Unstable Cyclopropene Dipolarophiles

A stereo- and regioselective 1,3-dipolar cycloaddition of the stable ninhydrin-derived azomethine ylide [2-(3,4-dihydro-2H-pyrrolium-1-yl)-1-oxo-1H-inden-3-olate, DHPO] to differently substituted cyclopropenes has been established. As a result, an efficient synthetic protocol was developed for the preparation of biologically relevant spiro[cyclopropa[a]pyrrolizine-2,2′-indene] derivatives. DHPO has proved to be an effective trap for such highly reactive and unstable substrates as parent cyclopropene, 1-methylcyclopropene, 1-phenylcyclopropene, and 1-halo-2-phenylcyclopropenes. It has also been found that 3-nitro-1,2-diphenylcyclopropene undergoes a nucleophilic substitution reaction in alcohols and thiols to afford 3-alkoxy- and 3-arylthio-substituted 1,2-diphenylcyclopropenes, which can be captured as corresponding 1,3-dipolar cycloadducts in the presence of DHPO. These new approaches provide a straightforward strategy for the synthesis of functionally substituted cyclopropa[a]pyrrolizine derivatives. The factors governing regio- and stereoselectivity have been revealed by means of quantum mechanical calculations (M11 density functional theory), including previously unreported Nylide-Hcyclopropene second-orbital interactions. The outcome of this work contributes to the study of 1,3-dipolar cycloaddition, as well as enriches chemistry of cyclopropenes and methods for the construction of polycyclic compounds with cyclopropane fragments.

CYCLOPROPENES-GENERATING DEVICES TO CONTROL RIPENING PROCESSES OF AGRICULTURAL PRODUCTS

Provided is a device for generation of cyclopropene compounds which is capable of achieving direct in situ preparation and application of cyclopropene compounds inhibiting the action of ethylene which accelerates the ripening process of plants, the device comprising a first storage part for storing precursors of cyclopropene compounds (“cyclopropene precursors”), a second storage part for storing reaction reagents which convert cyclopropene precursors into cyclopropene derivatives via chemical reaction, and a spray part for spraying the cyclopropene derivatives produced by the chemical reaction between the cyclopropene precursors and the reaction reagents.

Photoisomerization and photochemistry of matrix-isolated 3-furaldehyde

3-Furaldehyde (3FA) was isolated in an argon matrix at 12 K and studied using FTIR spectroscopy and quantum chemistry. The molecule has two conformers, with trans and cis orientation of the O=C-C=C dihedral angle. At the B3LYP/6-311++G(d,p) level of theory, the trans form was computed to be ca. 4 kJ mol-1 more stable than the cis form. The relative stability of the two conformers was explained using the natural bond orbital (NBO) method. In fair agreement with their calculated relative energies and the high barrier of rotamerization (ca. 34 kJ mol-1 from trans to cis), the trans and cis conformers were trapped in an argon matrix from the compound room temperature gas phase in proportion ～7:1. The experimentally observed vibrational signatures of the two forms are in a good agreement with the theoretically calculated spectra. Broad-band UV-irradiation (λ > 234 nm) of the matrix-isolated compound resulted in partial trans → cis isomerization, which ended at a photostationary state with the trans/cis ratio being ca. 1.85:1. This result was interpreted based on results of time-dependent DFT calculations. Irradiation at higher energies (λ > 200 nm) led to decarbonylation of the compound, yielding furan, cyclopropene-3-carbaldehyde, and two C3H4 isomers: cyclopropene and propadiene.

Cyclic versus linear isomers produced by reaction of the methylidyne radical (CH) with small unsaturated hydrocarbons

The reactions of the methylidyne radical (CH) with ethylene, acetylene, allene, and methylacety- lene are studied at room temperature using tunable vacuum ultraviolet (VUV) photoionization and time- resolved mass spectrometry. The CH radicals are prepared by 248 nm multiphoton photolysisof CHBr 3 at 298 K and react with the selected hydrocarbon i n a helium gas flow. Analysis of photoionization efficiency versus VUV photon wavelength permits isomer-specific detection of the reaction products and allows estimation of the reaction product branching ratios. The reactions proceed by either CH insertion or addition followed by H atom elimination from the intermediate adduct. In the CH + C 2 H 4 reaction the C 3 H 5 intermediate decays byH atom loss to yield 70(±8)percent allene, 30(±8)percent methylacetylene, and less than 10percent cyclopropene, in agreement with previous RRKM results. In the CH + acetylene reaction, detection of mai nly the cyclic C 3 H 2 isomer is contrary to a previous RRKM calculations that predicted linear triplet propargylene to be 90percent of the total H-atom coproducts. High-level CBS-APNO quantum calculations and RRKM calculations for the CH + C 2 H 2 reaction presented in this manuscript predict a higher contribution of the cyclic C 3 H 2 (27.0percent) versus triplet propargylene (63.5percent) than earlier predictions. Extensive calculations onthe C 3 H 3 and C 3 H 2 D system combined with experimental isotope ratios for the CD + C 2 H2 reaction indicate that H-atom-assisted isomerization in the present experiments is responsible for the remaining discrepancy between the new RRKM calculations and the experimental results. Cyclic isomers are also found to represent 30(±6)percent of the detected products in the case of CH + methylacetylene, together with 33(±6)percent 1,2,3- butatriene and 37(±6)percent vinylacetylene. The CH + allene reaction gives 23(±5)percent 1,2,3-butatriene and 77(±5)percent vinylacetylene, whereas cyclic isomers are produced below the detection limit in this reaction. The reaction exit channels deduced by comparing the product distributions for the aforementioned reactions are discussed in detail.

Crossed beam investigations of the reaction dynamics of O(3P) with allyl radical, C3H5

The nascent rovibrational distributions of the OH product from the newly observed exothermic reaction of O(3P)+C3H5→ C3H4+OH were studied. The atom-radical reaction dynamics was first probed through t

Intermolecular Pauson-Khand reactions of cyclopropane: A general synthesis of cyclopentanones

(equation presented) The Pauson-Khand reaction of cyclopropene with a variety of terminal alkynes has been studied. The best reaction conditions involve NMO activation in CH2Cl2 at -35 °C. In this way, 3-substituted-bicyclo[3.1.0]hex-3-en-2-ones have been obtained in good to excellent yields. As a synthetic application, several types of substituted cyclopentenones have been prepared from these cycloadducts by protocols involving conjugate addition and reductive ring opening.

UV photodissociation dynamics of allyl radical by photofragment translational spectroscopy

The photodissociation of the allyl radical was studied by photofragment translational spectroscopy following excitation to the C(pver-tilde) (22B1) and A(over-tilde)(12B1) states. At 248 nm excitation, two different primary channels were detected: H-atom loss and CH3 elimination. The overall shape of the P(ET) for the H-atom loss channel suggests a statistical dissociation from the ground potential energy surface of the C3H5 system.