53897-30-6

Usage

Uses

Used in Chemical Production:
2,3-Epoxy-4,4-dimethylpentane is used as a chemical intermediate for the production of other chemicals. It plays a crucial role in the synthesis of various compounds, contributing to the versatility and functionality of the end products.
Used in Organic Synthesis:
In the field of organic synthesis, 2,3-Epoxy-4,4-dimethylpentane is utilized as a solvent or reagent. Its unique properties allow it to facilitate specific chemical reactions, enhancing the efficiency and yield of the synthesis process.
Used in Industrial Applications:
2,3-Epoxy-4,4-dimethylpentane is employed in various industrial applications due to its chemical properties. Its versatility as a solvent or reagent makes it valuable in the manufacturing of different products across various industries.
It is important to handle 2,3-Epoxy-4,4-dimethylpentane with care, as it can cause skin and eye irritation and may be harmful if inhaled or ingested. Proper storage and disposal are necessary to prevent environmental contamination.

Upstream product

• 762-63-0 cis-4,4-dimethyl-2-pentene 
• 690-08-4 (E)-4,4-dimethyl-2-pentene 

Relevant academic research and scientific papers

Activation parameters for the epoxidation of substituted cis/trans pairs of 1,2-dialkylalkenes by dimethyldioxirane

The first activation parameter data for the reaction of dimethyldioxirane (1) with five cis/trans pairs of alkenes are reported. The epoxidation of cis-1,2-dialkylalkenes (2cis: R1 = Me, R2 = iPr; 3cis: R1 = Me, R2 = tBu; 4cis: R1 = R2 = Et; 5cis: R1 = Et, R2 = iPr; 6cis: R1 = Et, R2 = tBu) and trans-1,2-dialkylalkenes (2trans: R1 = Me, R2 = iPr; 3 trans: R1 = Me, R2 = tBu; 4trans: R1 = R2 = Et; 5trans: R1 = Et, R2 = iPr; 6trans: R1 = Et, R2 = tBu) by 1 produced the corresponding epoxides, quantitatively and stereospecifically, as the sole observable products. Activation parameters of the epoxidation of the five pairs of alkenes, 2cis-6cis and 2trans-6trans, by 1 were determined using the Arrhenius method. Enhanced selectivity for cis- vs. trans-alkene epoxidation was observed at lower temperatures. In general, the ΔG? terms were larger and showed more variability for the reaction of 1 with trans-alkenes as compared to those for the corresponding cis isomers. The ΔH? terms mirrored trends observed in ΔG ? because ΔS? terms for all ten of the compounds were roughly identical. The ΔΔG? values, a comparison of the trans to the cis isomer data, yielded positive values of 1.2 to 1.8 kcal/mol for the five sets of data and appeared to be dependent on relative steric interactions. The experimental activation parameter data, consistent with predictions from ab initio calculations based on a spiro transition-state model, showed that the lower reactivity of trans-alkenes is due to enthalpy factors. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

The Mechanism of Solvolysis of 2,2-Dimethyl-3-pentyl and 1-(1-Adamantyl)propyl Sulfonates

Solvolysis rates, alpha and beta deuterium isotope rate effects and product yields have been determined for some 1-(1-adamantyl) propyl sulfonate esters, 4, in some ethanol-water, trifluoroethanol-water and hexafluoroisopropyl alcohol-water mixtures. For comparison, similar measurements have been made for solvolysis of 2,2-dimethyl-3-pentyl sulfonates, 5. For the esters 5, the alpha-d and beta-d2 effects vary little with solvent in the ranges of 1.164-1.165 and 1.215-1.241, respectively, and only small yields of unrearranged products are formed; it is concluded that the mechanism involves rate determining formation of the secondary cation-ion pair followed by rapid rearrangement. For the adamantyl analogs, 4, the alpha-d effects vary in the different solvents from 1.162 to 1.213 and the beta-d2 effects vary from 1.339 to 1.649; significant yields of unrearranged and Wagner-Meerwein rearranged (ring expansion) products are formed. The steady state treatment, which had been used previously to fit the results for 1-(1-adamantyl)ethyl esters, was applied to the results for 4; a mechanism which involves partially reversible ionization to the intimate ion-pair followed by competing elimination and solvent separation, to give the substitution products, fits the results reasonably well.

Epoxidation by Dimethyldioxirane: Electronic and Steric Effects

The reaction of dimethyldioxirane (1) with a series of di- and monosubstituted alkenes 2-17 produced the corresponding epoxides in high yield.A kinetic study of the epoxidation of 2-17 by 1 in dried acetone showed the reaction to be of the first order with respect to both alkene and dioxirane.For certain cis/trans-dialkylalkenes, the cis compounds were found to be of ca. 10-fold greater reactivity than the corresponding trans isomers.However, cis/trans pairs of alkenes with phenyl substituents were found to be of similar reactivity.A kinetic study on the reaction of a series of substituted styrenes yielded an excellent LFER with a ρ value of -0.90.Addition of water to dioxirane reactions in acetone increased the observed rates of epoxidation.However, a tertiary allylic alcohol was found to undergo epoxidation slower than expected.The mechanistic implications of the results are discussed.