1927-59-9

Usage

Uses

Used in Chemical Reactions:
2-TERT-BUTOXYTETRAHYDROFURAN is used as a solvent for facilitating various chemical reactions. Its properties allow it to dissolve a wide range of substances, making it a versatile component in the synthesis of different compounds.
Used in Organic Synthesis:
In the realm of organic synthesis, 2-TERT-BUTOXYTETRAHYDROFURAN serves as a source of 2-tetrahydrofuranyl radicals. These radicals are crucial in the formation of complex organic molecules, contributing to the structural diversity and functional groups present in synthesized products.
Used as a Protecting Group in Organic Chemistry:
2-TERT-BUTOXYTETRAHYDROFURAN is utilized as a protecting group for alcohols, playing a critical role in organic chemistry. It prevents the alcohol functional groups from participating in unwanted side reactions during the synthesis process, thereby ensuring the desired product formation and maintaining the integrity of the chemical structure.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, given its applications in organic synthesis and as a protecting group, 2-TERT-BUTOXYTETRAHYDROFURAN can be inferred to have uses in the pharmaceutical industry for the development and production of various drugs, where its properties aid in the synthesis of complex molecular structures.
Safety Precautions:
Given its moderately hazardous nature, 2-TERT-BUTOXYTETRAHYDROFURAN necessitates the implementation of safety precautions during its use. This includes wearing protective gloves to prevent skin contact and eyewear to shield the eyes from potential hazards. Proper handling and disposal methods should be adhered to, in accordance with safety guidelines and regulations.

InChI:InChI=1/C8H16O2/c1-8(2,3)10-7-5-4-6-9-7/h7H,4-6H2,1-3H3

Upstream product

• 109-99-9 tetrahydrofuran 
• 614-45-9 tert-Butyl peroxybenzoate 
• 84210-61-7 perpentene-4 oate de tertiobutyle 
• 107671-70-5 7-(tert-butylperoxy)hept-1-ene 
• 85684-59-9 percarbonate de O,O-t-butyle et O-vinyle 
• 75-65-0 tert-butyl alcohol 
• 627-27-0 homoalylic alcohol 
• 126248-80-4 tert-butyl n-pentyl peroxide 
• 1191-99-7 2,3-dihydro-2H-furan 

Downstream Products

• 75-65-0 tert-butyl alcohol 

Relevant academic research and scientific papers

Bronsted acid catalyzed asymmetric SN2-Type O-alkylations

Bridging the gap: Bronsted acids catalyze an intramolecular S N2-type alkylation of alcohols with ethers by bridging a pentacoordinate transition state, thus simultaneously activating both the leaving group and nucleophile (see scheme). Density functional calculations provide detailed insight into the course of the reaction and the transition-state structure.

Amberlyst-15-catalyzed one-pot synthesis of 2-aryltetrahydrofurans from tetrahydrofuran

A simple one-step route for the conversion of naphthols and phenols with tetrahydrofuran into corresponding 2-aryltetrahydrofurans using Amberlyst-15 as a catalyst is reported. This is the first example of the acid-mediated formation and rearrangement reactions of tetrahydrofuranyl ethers prepared from the tetrahydrofuran and aromatic/aliphatic hydroxy compounds.

The selective functionalization of saturated hydrocarbons. Part 40. Aspects of Fe(II) based peroxide fragmentation in pyridine solution

The Haber-Weiss mechanism does not apply to the Fe(II) induced fragmentation of primary and secondary hydroperoxides in pyridine. However, it does apply to tertiary hydroperoxides. Steric bulk is an important factor in Fe(II) induced dialkyl peroxide decomposition in pyridine. On the contrary in tetrahydrofuran a different relatively unhindered electron transfer process predominates where the Fe(II) becomes a catalyst.

Decomposition Induite de Peroxydes Acetyleniques

Acetylenic peroxides react as radicals in good hydrogen-donor solvents.Addition to the triple bond leads to monoadducts and attack on the O-O bond gives unsaturated acetals.The intermediate vinyl radical obtained in the first case does not seem to lead to homolytic intramolecular substitution.Unlike their ethylenic homologous these compounds are not unsaturated heterocycle precursors.

Catalytic oxidation of homoallylalcohols to α-alkoxytetrahydrofurans by a Pd-nitro complex and molecular oxygen

Various homoallylalcohols were highly regioselective oxidized with molecular oxygen at the terminal carbon to afford cyclic acetals (α-alkoxytetrahydrofurans) using PdNO2CL(CH3CN)2 as catalyst in the presence of CuCL2 and t-butanol or isopropanol.

Direct Facile Tetrahydrofuranylation Of Alcohols Through Radical Coupling With (Bu4N)2S2O8

Primary, secondary and tertiary alcohols can be converted in excellent yields into their 2-tetrahydrofuranyl-ethers in the presence of n-tetrabutylammonium peroxydisulfate under nearly neutral condition in tetrahydrofuran.

Cerium(IV)-Mediated Synthesis of Tetrahydrofuranyl Ethers

The reaction of tetrahydrofuran with an alcohol in the presence of ceric triethylammonium nitrate provides a convenient and general procedure for protecting the hydroxyl function.Tetrahydrofuranyl ethers of primary, secondary and tertiary alcohols were obtained in good yields.

DEPLACEMENTS HOMOLYTIQUES INTRAMOLECULAIRES . 12 - DECOMPOSITION INDUITE DE PEROXYDES ETHYLENIQUES : INFLUENCE DE LA LONGUEUR DE LA CHAINE

Products analyses of the thermolyses of the peroxides CH2=CH-(CH2)nOOtBu, 1, (n=1-5) showed that an induced decomposition of 1 occurred for n=1,2,3,4.Free radical additions of THF, carbon tetrachloride, bromotrichloromethane to 1 have been performed at lower temperature; they allowed, through the isolation of an adduct peroxide, at least in one case for each peroxide, to prove that a two-steps mechanism (addition of radical Z. to the double bond, intramolecular homolytic displacement) is involved in the induced decomposition of 1.The order of magnitude of the rate constants of these SHi reactions could be estimated.

Deplacements homolytiques intramoleculaires. 2. Decomposition du perpentene-4 oate de tert-butyle dans les ethers

The thermolysis of tert-butyl perpent-4-enoate 1 in THF led to several compounds; the main product, 5-(2-tetrahydrofuryl)-4-pentanolide (yield 42percent) comes from an induced decomposition of the perester occuring with the addition of 2-tetrahydrofuryl radical to the double bond.A similar reaction was performed at a lower temperature, using butyl perdicarbonate as initiator, but did not define the mechanism (concerted or two-step).The thermolysis of 1 in ethers (THP, oxepane, 1,4-dioxane, dipropyl ether) appears to be a useful synthetic tool: several new γ-lactones have been obtained in this way.

Obtention d'aldehydes γ-fonctionnels au cours de la thermolyse du percarbonate de O,O-t-butyle et O-vinyle en solution

Owing to its peroxyester group, O,O-tert-butyl and O-vinyle peroxycarbonate may act as a free radical initiator in solution, but also, due to the presence of the vinylic insaturation, as a substrate for free radical addition reactions. - In such solvents as cumene which give free radicals unable to add to the double bond, the peroxycarbonate merely behaves as a vinyloxy radicals generator.It is thus possible to observe these radicals reacting either as formylmethyl radicals or as acetyl radicals. - In solvents such as cyclohexane which give free radicals able to add to the double bond, the reaction results in the substitution of formylmethyl groups to labile hydrogens of the solvent. - By applying the reaction to such compounds as ketones, ethers, acids and their derivatives, we could obtain γ-functional aldehydes (γ-ketoaldehydes, γ-oxaaldehydes and derivatives of succinaldehydic acids).These products are often difficult to prepare by other routes and until now only some of them have been described.