65146-94-3

Usage

Uses

Used in Chemical Research:
Cyclopropane-1,1-d2 is used as a research compound for studying reaction mechanisms and understanding the behavior of molecules in chemical reactions. The presence of deuterium atoms allows for the investigation of kinetic isotope effects, which can provide insights into reaction pathways and transition states.
Used in Spectroscopic Analysis:
Cyclopropane-1,1-d2 is utilized as a spectroscopic standard or analyte in various spectroscopic techniques, such as infrared (IR) and nuclear magnetic resonance (NMR) spectroscopy. The deuterium atoms in the compound can cause shifts in spectral peaks, enabling the identification and quantification of specific functional groups and structural features in complex mixtures.
Used in Isotope Labeling:
Cyclopropane-1,1-d2 serves as an isotope-labeled compound in experiments involving isotope labeling. This technique is valuable for tracking the movement and incorporation of specific atoms within chemical reactions, metabolic pathways, or environmental processes, providing valuable information on reaction mechanisms and metabolic fluxes.
Used in Material Science:
Cyclopropane-1,1-d2 may be employed in the development and characterization of new materials, such as polymers or catalysts. The incorporation of deuterium atoms can affect the material's properties, such as stability, reactivity, or mechanical strength, offering a means to fine-tune and optimize material performance for specific applications.

Upstream product

• 74-85-1 ethene 
• 3591-34-2 1,1-dibromocyclopropane 
• 261381-51-5 3-[dimethyl(m-trifluoromethylphenyl)silyl][1,1-2H₂]propyl tosylate 
• 261381-50-4 3-[p-methoxyphenyl(dimethyl)silyl][1,1-2H₂]propyl tosylate 
• 261381-49-1 3-(dimethylphenylsilyl)[1,1-2H₂]propyl tosylate 
• 75-89-8 2,2,2-trifluoroethanol 
• 64-17-5 ethanol 

Relevant academic research and scientific papers

The γ-silicon effect. IV. The solvolysis mechanism of 3-(aryldimethylsilyl)propyl p-toluenesulfonates

The solvolysis of 3-(aryldimethylsilyl)propyl p-toluenesulfonates was described based on the effects of substituents, solvents, and deuterium isotope, in comparison with the γ-silyl-assisted solvolysis of 3-(aryldimethylsilyl)-2,2-dimethylpropyl toluenesulfonates. The solvent effect on the simple γ-silyl assisted system showed the nucleophilic assistance of solvent, but failed to correlate linearly with the extended Winstein-Grunwald equation, substantiating that the reaction should not proceed through either the formation of the cation intermediate of the SN2 mechanism. This suggested that the reaction occurs in competition between γ-silyl-assisted (kSi) and solvent-assisted (ks) pathways, and that the competition ratio varies with solvents and with aryl substituents. Product analysis revealed that the former pathway gave only cyclopropane and the latter gave only the substitution products. Using product ratios, the overall rate constant (kt) value could be dissected into the partial rate constants kSi and ks for the two pathways. The effects of aryl substitutes at the γ-silyl atom on kSi pathway were correlated with unexalted σ°(normal substituent constant) parameter, giving the ρ values of -1.0 in 60E and -1.32 in 97Tw, and reflecting the delocalization of incipient carbocationic charge by participation of the Si-Cγ bond. The substituent effects on the ks pathway were negligible, which is in line with the remote reaction center in the concerted SN2 mechanism.

The γ-silicon effect on solvolyses of the 3-(aryldimethylsilyl)propyl system

The γ-silicon effects in solvolyses were studied mechanistically on 3-(aryldimethylsilyl)propyl tosylates in various solvents based on the substituent effects. The mechanism can be described as competing reactions of the γ-silyl-assisted (kSi) and the solvent-assisted (ks) pathways. Copyright

Inter- and intramolecular experimental and calculated equilibrium isotope effects for (silox)2((t)Bu3SiND)TiR + RH (silox = (t)Bu3SiO): Inferred kinetic isotope effects for RH/D addition to transient (silox)2Ti

Intermolecular equilibrium isotope effects (EIEs) were measured (26.5 °C) and calculated for (silox)2((t)Bu3SiND)TiR(D) (1-ND-R(D)) + R(H)H ? (silox)2((t)Bu3SiNH)TiR(H) (1-R(H)) + R(D)D: R(H)H/R(D)D = CH4/

Cyclobutanone-3,3-d2 and trimethylene-2,2-d2

An efficient five-step synthesis of cyclobutanone-3,3-d2 is reported. This ketone gives direct access through laser flash photolysis to the trimethylene-2,2-d2 diradical. The life-time of trimethylene-2,2-d2 provides an experimental showing that trimethylene and deuterium-labeled trimethylene diradicals decay to form cyclopropanes, rather than propenes.

Reactions of FeCH3+ and CoCH3+ with Aliphatic Alkenes and Alkynes in the Gas Phase

The gas-phase reactions of FeCH3+ and CoCH3+ with a variety of alkenes are described by using Fourier transform mass spectrometry (FTMS).FeCH3+ is unreactive with ethene, while CoCH3+ reacts with ethene to yield the allyl product CoC3H53.This reaction presumably proceeds by initial methyl migratory insertion into coordinated ethene to form a Co(propyl)+ complex which subsequently dehydrogenates.Reactions with alkenes containing labile hydrogens α to the double bond proceed by initial elimination of methane to form an activated ?-allyl complex which may subsequently decompose further.Both FeCH3+ and CoCH3+ undergo migratory insertion into coordinated butadiene generating a ?-pentenyl complex which undergoes dehydrogenation.In addition, both FeCH3+ and CoCH3+ appear to insert into ethyne, generating a vinyl species which dehydrogenates to form MC3H3+.These results suggest the following order for methyl migratory insertation into C-C multiple bonds: butadiene ca. ethyne > ethene.Decomposition of M(C5H9)+ species proceeds by initial skeletal rearrangement to a linear structure followed by dehydrocyclization to generate M-c-C5H5+.A stable Co(pentadienyl)+ species was generated and is distinguishable from the corresponding Co(cyclopentyl)+ complex by H/D exchange with deuterium.Finally, D0(Fe+-pentadienyl) is found to exceed 70 +/- 6 kcal/mol and D0(Co+-pentadienyl) exceeds 62 +/- 5 kcal/mol.