81395-27-9

Upstream product

• 589-15-1 1-bromomethyl-4-bromobenzene 
• 100-51-6 benzyl alcohol 
• 1122-91-4 4-bromo-benzaldehyde 
• 27691-43-6 1-(benzylsulphanyl)-4-Nitrobenzene 
• 873-75-6 4-bromobenzenemethanol 
• 100-39-0 benzyl bromide 
• 14642-79-6 benzyloxy-trimethylsilane 
• 2785-29-7 benzyl potassium 

Downstream Products

• 1401009-27-5 C₁₈H₁₈O 
• 163680-70-4 (4-benzyloxymethylphenyl)boronic acid 
• 443693-54-7 4-Benzyloxymethyl-phenol 

Relevant academic research and scientific papers

Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.

Developing benign syntheses using ion pairsviasolvent-free mechanochemistry

Solvent-free mechanochemical conditions have been developed to investigate the significance of ion pairing and the use of weak bases for driving forward nucleophilic substitution reactions. This approach takes advantage of the lack of solvent shells to in

Reductive Etherification via Anion-Binding Catalysis

Reductive condensations of alcohols with aldehydes/ketones to generate ethers are catalyzed by a readily accessible thiourea organocatalyst that operates in combination with HCl. 1,1,3,3-tetramethyldisiloxane serves as a convenient reducing reagent. This strategy is applicable to challenging substrate combinations and exhibits functional group tolerance. Competing reductive homocoupling of the carbonyl component is suppressed.

Cosolvent-Promoted O-Benzylation with Silver(I) Oxide: Synthesis of 1′-Benzylated Sucrose Derivatives, Mechanistic Studies, and Scope Investigation

A cosolvent-promoted O-benzylation strategy with Ag2O was developed. The cosolvent consisting of CH2Cl2 and n-hexane can not only improve the reaction solubility for carbohydrates but also increase the benzylation efficiency. The formation of byproducts is greatly inhibited in the developed method. This method is simple, mild, and highly effective, and numerous 1′-benzylated sucrose derivatives were prepared including a photoreactive (trifluoromethyl)phenyldiazirine-based sucrose. The mechanisms of benzylation with primary and secondary benzyl bromides were also elaborated. Furthermore, the application scope with alcohols, glucose, and ribose derivatives was investigated.

Synthesis of ethers from carbonyl compounds by reductive etherification catalyzed by iron(III) and silyl chloride

A simple iron- and silyl chloride catalyzed method for the preparation of symmetrical and nonsymmetrical ethers is presented. Various aldehydes and ketones were reductively etherified by using triethylsilane as a reducing agent in the presence of 2 mol% of iron(III) oxo acetate and 8 mol% of chloro(trimethyl)silane. The reactions can be carried out at ambient temperatures and pressures with ethyl acetate as the solvent.

PESTICIDAL SUBSTITUTED PHENYLETHERS

The invention relates to the use of phenylether derivatives of formula (I), to compositions thereof for the control of pests, including arthropods and helminths.

Radical substitution with azide: TMSN3-PhI(OAc)2 as a substitute of in3

TMSN3 and PhI(OAc)2 were found to promote high-yield azide substitution of ethers, aldehydes and benzal acetals. The reaction is fast and occurs at zero to ambient temperature in acetonitrile. However, it is essential for the reaction that TMSN3 is added subsequent to the mixture of PhI(OAc)2 and the substrate. A primary deuterium kinetic isotope effect was found for the azidonation of benzyl ethers both with TMSN3-PhI(OAc)2 and with IN3. Also a Hammett free energy relationship study of this reaction showed good correlation with σ+ constants giving with ρ-values of -0.47 for TMSN 3-PhI(OAc)2 and -0.39 for IN3. On this basis a radical mechanism of the reaction was proposed. The Rayal Society of Chemistry 2005.

A highly efficient method for the reductive etherification of carbonyl compounds with triethylsilane and alkoxytrimethylsilane catalyzed by iron(III) chloride

Facile reductive etherification of carbonyl compounds can be conveniently performed by reaction with triethylsilane and alkoxytrimethylsilane catalyzed by iron(III) chloride. The corresponding alkyl ethers, including benzyl and allyl ethers, of the reduced alcohols were obtained in good to excellent yields under mild reaction conditions.

Skeletal Rearrangements on Chemical Ionization of Dibenzyl Ether and Derivatives

Protonated molecular ions of dibenzyl ether, formed by chemical ionization using hydrogen and isobutane as reagent gases, undergo skeletal rearrangements to lose water and formaldehyde, both in the ion source and the flight path.The rearrangements have been elucidated by deuterium labelling and chemical substitution.The water lost contains the reagent proton and an aromatic hydrogen atom, and the aromatic hydrogen atoms have been shown to be mobile prior to the reaction.It is proposed that the skeletal rearrangement for water loss is initiated by protonation on the other oxygen atom, followed by benzyl migration.The formaldehyde loss contains benzylic hydrogen atoms exclusively, and it is proposed that the skeletal rearrangement is preceded by hydrogen rearrangement of an oxygen protonated molecular ion to a ring protonated molecular ion.Daughter ion structures are supported by comparisons of their collision induced dissociation spectra with those of isomeric ions prepared by alternative routes.