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Prilezhaev reaction

The Prilezhaev reaction is the epoxidation of alkenes using peroxy acids to form epoxides (oxiranes).^[1]^[2] Discovered in 1909 by Russian chemist Nikolai Alexandrovich Prilezhaev, the reaction involves the electrophilic addition of an oxygen atom from the peroxy acid to the carbon-carbon double bond of the alkene, proceeding through a concerted "butterfly" transition state that preserves the stereochemistry of the starting alkene.^[2]^[1] The most commonly employed reagent is meta-chloroperoxybenzoic acid (mCPBA), though alternatives such as peracetic acid, peroxybenzoic acid, or magnesium monoperphthalate are also used, typically in neutral organic solvents like dichloromethane.^[1]^[3] This transformation is highly versatile, applicable to a broad range of alkenes including electron-rich, electron-poor, and sterically hindered substrates, and it tolerates many functional groups such as alcohols, ethers, and halides without interference.^[3] The reaction's stereospecific syn addition makes it valuable for synthesizing enantiomerically enriched epoxides when starting from chiral alkenes, and it exhibits excellent regioselectivity influenced by directing groups like hydroxyl moieties via hydrogen bonding.^[1]^[3] Epoxides produced via this method serve as key intermediates in the synthesis of pharmaceuticals, agrochemicals, and materials, such as glycols, polyoxoalkylenes for detergents and lubricants, and complex natural products.^[2] Modern variants include continuous flow processes, ultrasound-assisted epoxidations for improved yields, and phase-vanishing techniques to enhance safety and efficiency with hazardous peracids.^[3]

History

Discovery

Nikolai Alexandrovich Prilezhaev, a Russian chemist working at the Warsaw Polytechnic Institute, first reported the epoxidation of alkenes using perbenzoic acid in 1909. This breakthrough introduced a selective method for converting carbon-carbon double bonds into oxiranes, marking a significant advancement in organic synthesis. Prilezhaev's work focused on the use of organic peroxides, which he termed "superoxides," to achieve this transformation under relatively mild conditions. The original publication appeared in the Berichte der deutschen chemischen Gesellschaft, detailing the oxidation of isolated double bonds to oxiranes while leaving other functional groups intact, a level of selectivity not readily achievable with earlier oxidants like chromic acid or potassium permanganate. Prilezhaev described experiments with simple alkenes, including styrene and cyclohexene, where perbenzoic acid in ether or chloroform solutions at low temperatures yielded the corresponding epoxides in good yields, often isolating them as crystalline derivatives. These initial studies demonstrated the reaction's potential for preparing pure epoxides from unsaturated compounds. This discovery emerged in the broader context of pre-World War I organic chemistry, a period of rapid progress in Russia and Europe where chemists were exploring peroxides as versatile reagents for selective oxidations. Prilezhaev's contributions built on emerging knowledge of peracids, positioning them as key tools amid growing interest in oxygen heterocycles and reaction mechanisms. His 1909 report laid the foundation for subsequent developments in epoxidation chemistry.

Developments

Following the initial discovery, significant advancements in the Prilezhaev reaction occurred in the 1930s with the introduction of peracetic acid as a safer alternative to earlier peracids. Böeseken, Smit, and Gaster demonstrated its efficacy for epoxidizing unsaturated compounds, particularly through in situ generation from acetic acid and hydrogen peroxide, which minimized explosion risks and improved practicality for laboratory use.^[4] This approach yielded high conversions for a range of olefins, such as fatty acid derivatives, and became a standard method for preparing epoxy oils.^[5] In the 1940s and 1950s, further refinements focused on peracids suited to sensitive substrates. Swern and collaborators advanced the use of performic acid, generated in situ from formic acid and hydrogen peroxide, which provided milder conditions and higher yields for acid-labile olefins compared to peracetic acid, as detailed in their studies on 1-olefin epoxidations.^[6] Concurrently, the development of pertrifluoroacetic acid by Emmons et al. in 1955 offered enhanced reactivity for sterically hindered or electron-deficient alkenes, enabling epoxidations that were inefficient with less electrophilic peracids and improving overall substrate tolerance.^[7] These innovations collectively expanded the reaction's utility in organic synthesis during this period. The stereospecific nature of the Prilezhaev reaction, involving retention of cis/trans alkene geometry in the resulting epoxide, gained early recognition in the 1950s through systematic studies. Swern's comprehensive analysis confirmed that cis-olefins exclusively yield cis-epoxides and trans-olefins yield trans-epoxides, underscoring the concerted mechanism and influencing subsequent mechanistic interpretations. Naming conventions for the reaction evolved post-World War II, with the Russian transliteration "Prilezhaev" becoming standardized in English-language literature, superseding the earlier German form "Prileschajew" used in pre-war European publications.^[1] A pivotal consolidation of these developments appeared in Swern's 1953 chapter in Organic Reactions, which reviewed peracid epoxidations, summarized reagent advancements, and highlighted synthetic scope up to that time.^[8]

Reaction

General Scheme

The Prilezhaev reaction involves the epoxidation of an alkene using an organic peracid, resulting in the formation of an epoxide (oxirane) and a carboxylic acid as the byproduct.^[3] The general stoichiometry is 1:1 between the alkene and peracid, with the core transformation represented by the balanced equation:

\mathrm{R_2C=CR_2 + R'CO_3H \rightarrow} \begin{array}{c} \ce{O} \\ / \backslash \\ \mathrm{R_2C--CR_2} \end{array} + R'CO_2H

where \mathrm{R_2C=CR_2} denotes a generic alkene and \mathrm{R'CO_3H} a peracid.^[3] A representative example is the reaction of trans-2-butene with meta-chloroperoxybenzoic acid (mCPBA), yielding trans-2,3-epoxybutane and meta-chlorobenzoic acid.^[9] In this process, the carboxylic acid serves as the leaving group from the peracid, often necessitating purification steps to isolate the epoxide product.^[3] This transformation is classified as an electrophilic addition to the alkene double bond, functioning as an oxygen transfer process that preserves the alkene's stereochemistry.^[2]

Reagents and Conditions

The Prilezhaev reaction primarily utilizes m-chloroperoxybenzoic acid (mCPBA) as the key reagent, a commercially available peracid noted for its relative stability under ambient conditions and high solubility in organic solvents such as dichloromethane (CH₂Cl₂) or hexane.^[1] This reagent is typically supplied at 70-77% purity with water as a stabilizer to mitigate explosive risks associated with concentrated peracids. Alternative peracids include peracetic acid, often generated in situ by mixing hydrogen peroxide with acetic acid, which is suitable for large-scale applications due to its low cost; performic acid, prepared similarly from hydrogen peroxide and formic acid and preferred for water-soluble alkenes; and perbenzoic acid, the originally employed reagent that is less stable and requires freshly prepared solutions.^[10] These alternatives are selected based on substrate solubility and the need to avoid byproduct interference from m-chlorobenzoic acid.^[11] The reaction proceeds in inert, non-nucleophilic solvents including dichloromethane, chloroform, hexane, benzene, or carbon tetrachloride to prevent side reactions with the peracid.^[12] Typical conditions involve temperatures from -10°C to 60°C, often starting at 0°C and warming to room temperature, with reaction durations of 1 to 24 hours depending on substrate reactivity, yielding epoxides in 60-80% isolated yields for most alkenes. Safety considerations are paramount, as peracids like mCPBA are strong oxidants that can ignite flammable materials or explode from shock, friction, contamination, or excessive heating under confinement; storage at 0-5°C in the provided aqueous suspension is recommended, and reactions should be conducted behind blast shields with minimal scale initially. Post-reaction workup involves cooling the mixture to 0°C, washing with aqueous sodium bisulfite (NaHSO₃) or sodium thiosulfate (Na₂S₂O₃) solution to quench excess peracid by reducing it to the corresponding carboxylic acid, extraction of the epoxide with an organic solvent, and washing with saturated aqueous sodium bicarbonate to remove acidic impurities.^[11]^[9]

Mechanism

Concerted Pathway

The Prilezhaev reaction proceeds via a concerted mechanism involving the stereospecific syn addition of the peracid's electrophilic oxygen to the alkene, resulting in the formation of an epoxide without the involvement of discrete intermediates.^[1] This process is characterized by a single transition state where bond formation and cleavage occur synchronously, preserving the alkene's stereochemistry and yielding cis-epoxides from cis-alkenes and trans-epoxides from trans-alkenes. The mechanism, first elucidated by Bartlett in 1950, features a "butterfly" spiro transition state geometry in which the peracid and alkene align with the O-O bond perpendicular to the double bond plane, resembling the wings of a butterfly.^[1] In the key steps of this concerted pathway, the π electrons of the alkene act as a nucleophile, attacking the σ* orbital of the peracid's O-O bond, while simultaneously the O-O bond breaks and two new C-O bonds form to generate the epoxide ring.^[1] Concurrently, the carboxylic acid moiety departs as a neutral leaving group, completing the oxygen transfer in one step. The absence of carbocation or radical intermediates in this process accounts for the high stereospecificity observed, as there is no opportunity for rotation or rearrangement around the original double bond. Activation parameters for the reaction are consistent with a pericyclic-like concerted process, featuring a low activation energy of approximately 15-20 kcal/mol, which facilitates efficient epoxidation under mild conditions. The peracid adopts a conformation stabilized by intramolecular hydrogen bonding between the O-H group and the carbonyl oxygen, polarizing the O-O bond and contributing to the overall synchronicity of the pathway.^[1]

Electronic Interactions

The reactivity and regioselectivity of the Prilezhaev reaction are fundamentally governed by frontier molecular orbital (FMO) interactions between the alkene and peracid reactants. The primary interaction involves the highest occupied molecular orbital (HOMO) of the alkene, its π orbital, donating electron density to the lowest unoccupied molecular orbital (LUMO) of the peracid, specifically the σ* orbital of the O-O bond. This overlap facilitates the concerted transfer of the electrophilic oxygen atom. A secondary interaction occurs between the HOMO of the peracid, consisting of the non-bonding lone pair (n_O) on the transferring oxygen atom perpendicular to the molecular plane, and the π* LUMO of the alkene, which stabilizes the approach and contributes to the reaction's stereospecificity.^[13] These FMO considerations underscore the peracid's role as a soft electrophile, which preferentially epoxidizes electron-rich alkenes due to enhanced HOMO-LUMO overlap. Experimental evidence from Hammett correlations supports this: for substituents on aromatic alkenes, a negative ρ value (ρ ≈ -1.3) indicates that electron-donating groups on the alkene accelerate the reaction by raising the π HOMO energy. In contrast, for substituents on perbenzoic acids, a positive ρ value (ρ ≈ +1.4) demonstrates that electron-withdrawing groups on the peracid lower the σ* O-O LUMO energy, thereby increasing reactivity and confirming the electrophilic character of the oxygen delivery.^[14] Density functional theory (DFT) computations at the B3LYP/6-31G(d,p) level further validate these electronic interactions, depicting an asynchronous but concerted transition state where the forming C-O bonds are slightly longer than the breaking O-O bond, with the energy barrier typically around 15-16 kcal/mol for simple alkenes like ethylene. These studies emphasize how the FMO-driven charge transfer in the transition state aligns with the observed regioselectivity, favoring attack at the more electron-rich carbon of unsymmetrical alkenes. Secondary electronic effects, such as intramolecular hydrogen bonding in the peracid, provide additional stabilization. This interaction is particularly influential in directing the spiro-like approach of the peracid to the alkene double bond.

Scope and Selectivity

Substrate Compatibility

The Prilezhaev reaction exhibits broad substrate compatibility with various alkenes, particularly those featuring isolated carbon-carbon double bonds. Electron-rich alkenes, such as enol ethers and those with electron-donating substituents like alkyl groups, undergo epoxidation at the fastest rates due to their enhanced nucleophilicity toward the electrophilic peracid oxygen. For instance, relative rates increase dramatically with alkyl substitution: ethylene serves as the baseline (relative rate = 1), while propene reacts 24 times faster, trans-2-butene 500 times faster, and 2-methyl-2-butene over 6,500 times faster.^[15] Enol ethers display even higher reactivity, with relative rates much greater than ethylene, highlighting the accelerating effect of donor substituents.^[16] In contrast, electron-poor alkenes, such as acrylates, react significantly more slowly (relative rates <0.1 compared to ethylene), though they still afford epoxides under standard conditions.^[17] The reaction tolerates a range of functional groups, including alcohols, ketones, and esters, which remain intact during epoxidation. It is selective for isolated C=C bonds, sparing aromatic rings and carbonyl groups that do not participate. Representative examples include cyclohexene, which provides the corresponding epoxide in 90% yield, and styrene, yielding 80%. Allylic alcohols also epoxidize effectively, with hydroxyl groups directing the epoxidation to the syn face via hydrogen bonding, though protection may be required in some cases to prevent side reactions with the hydroxyl group.^[1] Steric effects influence reactivity, with terminal and less substituted alkenes preferred over highly hindered ones. Tetrasubstituted alkenes, such as 2,3-dimethyl-2-butene (relative rate >6,500 vs. ethylene), react readily despite bulkiness, but yields can drop to around 50% for particularly sterically demanding substrates due to hindered approach of the peracid.^[15] Overall, these trends underscore the reaction's utility for a wide array of alkene structures in synthetic applications.

Limitations and Selectivity Issues

One significant limitation of the Prilezhaev reaction is its chemoselectivity, as peracids can react with other functional groups present in the substrate. Sulfides are readily oxidized to sulfoxides or sulfones, while tertiary amines form N-oxides under similar conditions.^[18] Additionally, ketones undergo Baeyer-Villiger oxidation to esters when subjected to forcing conditions with excess peracid.^[18] The reaction exhibits high regioselectivity for the alkene double bond, particularly in the presence of directing groups like hydroxyls that influence stereoselectivity through hydrogen bonding. For unsymmetrical alkenes, the epoxide formation is regiochemically defined without mixtures of isomers under standard conditions.^[1] Yields in the Prilezhaev reaction typically range from 60% to 80%, influenced by substrate reactivity and conditions, with carboxylic acid byproducts complicating purification and isolation processes.^[3] The inherent instability of peracids also introduces safety concerns, including explosive decomposition risks that restrict large-scale applications.^[19] Solvent choice affects reaction efficiency, with polar protic solvents such as methanol significantly slowing the rate—up to 10-fold compared to nonpolar solvents like hexane—due to disruption of the peracid's internal hydrogen bonding.^[17] The reaction lacks inherent stereoselectivity for asymmetric synthesis; achiral alkenes produce racemic epoxides with standard peracids, and achieving enantioselectivity requires rare chiral peracid variants, which are stoichiometrically limited and infrequently employed.^[20]

Applications

Organic Synthesis

The Prilezhaev reaction serves as a cornerstone in laboratory organic synthesis for generating epoxides from alkenes, which act as versatile intermediates for further transformations. These epoxides are commonly hydrolyzed under acidic conditions to afford vicinal diols, providing a stereospecific route to 1,2-diols with retention of alkene geometry. Additionally, epoxides derived from the reaction can undergo ring-opening with nitrogen nucleophiles, such as sodium azide followed by reduction and cyclization, to yield aziridines, which are valuable in constructing nitrogen-containing heterocycles for pharmaceutical targets. In the case of 2,3-epoxy alcohols, base-promoted Payne rearrangement facilitates migration of the epoxide to the 1,2-position, enabling access to allylic alcohols with inverted stereochemistry at the migrated carbon, thus enhancing synthetic flexibility in polyol assembly. Notable applications include the synthesis of prostaglandin analogs, where the Prilezhaev epoxidation using m-chloroperoxybenzoic acid (mCPBA) targets unsaturated side chains to install epoxides that direct subsequent stereoselective reductions and openings. In E. J. Corey's seminal total synthesis of prostaglandin F_2α, mCPBA-mediated epoxidation of a ketoalkene intermediate proceeded regioselectively, which was crucial for establishing the cyclopentane core's oxygenation pattern. Similarly, in steroid chemistry, the reaction enables selective oxidation of Δ⁵-double bonds in cholesterol derivatives. For instance, treatment of cholesterol with p-(methoxycarbonyl)perbenzoic acid in dichloromethane at 25°C affords a mixture of 5α,6α- and 5β,6β-epoxycholesterols, with the α-epoxide predominating in 73% yield alongside near-quantitative overall conversion, demonstrating high stereoselectivity influenced by solvent polarity.^[21] Cascade sequences leveraging Prilezhaev epoxides further highlight its utility, such as epoxidation followed by in situ ring-opening to generate polyols or amino alcohols in a single pot. One representative example involves mCPBA epoxidation of chiral allylic alcohols, trailed by nucleophilic opening with amines or thiols under mild conditions, affording β-hydroxy amino alcohols, ideal for alkaloid scaffolds. These mild conditions, typically at room temperature in aprotic solvents, tolerate a wide array of functional groups including esters, ketones, and alcohols without interference, making the reaction indispensable for complex molecule assembly.^[22]

Industrial and Analytical Uses

The Prilezhaev reaction plays a significant role in the industrial production of epoxidized vegetable oils, such as epoxidized soybean oil, which serve as plasticizers, stabilizers for polyvinyl chloride, and components in surface coatings and epoxy resin formulations.^[23] These epoxides are generated by treating the double bonds in triglycerides with percarboxylic acids, typically formed in situ from hydrogen peroxide and carboxylic acids like acetic or formic acid, under acidic conditions.^[23] In the fragrance industry, the reaction is employed to produce limonene oxide from limonene, a terpene abundant in citrus oils, via in situ generation of performic or peracetic acid; this epoxide imparts woody and citrus notes and acts as an intermediate for polymers like poly(limonene carbonates).^[24] For pharmaceutical applications, the Prilezhaev reaction using m-chloroperoxybenzoic acid (mCPBA) is utilized to synthesize epoxide intermediates for active pharmaceutical ingredients, particularly antifungal agents such as efinaconazole, ravuconazole, isavuconazole, and albaconazole, where terminal alkenes are converted to epoxy alcohols with moderate diastereoselectivity.^[25] Scale-up of the reaction often employs continuous flow processes with in situ peracid generation, such as peracetic acid from hydrogen peroxide and acetic acid, to mitigate explosion risks associated with peracid accumulation and enable safe production of epoxides from alkenes, including those derived from vegetable oils.^[26] These flow systems have been applied to epoxidize used cooking oils, achieving high conversions while addressing the exothermic nature of the reaction.^[27] Analytically, the Prilezhaev reaction facilitates the determination of double bond geometry in unsaturated fatty acids from vegetable oils, such as safflower, linseed, walnut, and poppy seed oils, by epoxidizing alkenes with mCPBA followed by hydrolysis and analysis via liquid chromatography-high-resolution mass spectrometry; this distinguishes cis and trans isomers through diagnostic fragment ions and retention times, with enzymatic hydrolysis preferred over chemical methods to avoid isomerization artifacts.^[28] An industrial variant involves performic acid, generated in situ from hydrogen peroxide and formic acid, for the epoxidation of allyl alcohol to glycidol, a key intermediate in epoxy resin production and as a stabilizer for vinyl polymers.^[29] While mCPBA remains viable for ton-scale epoxidations due to its selectivity, its thermal instability limits broader adoption, prompting a shift toward greener hydrogen peroxide-based protocols that reduce waste and enhance sustainability in large-scale operations.^[26]^[30]

References

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