940-44-3Relevant academic research and scientific papers
Synthesis of Benzyl Alkyl Ethers by Intermolecular Dehydration of Benzyl Alcohol with Aliphatic Alcohols under the Effect of Copper Containing Catalysts
Bayguzina,Gimaletdinova,Khusnutdinov
, p. 1148 - 1155 (2018/10/24)
Synthesis of benzyl alkyl ethers was performed in high yields by intermolecular dehydration of benzyl and primary, secondary, tertiary alcohols under the effect of copper containing catalysts. The formation of benzyl alkyl ethers occurs with participation of benzyl cation.
Synthesis of bimetallic Zr(Ti)-naphthalendicarboxylate MOFs and their properties as Lewis acid catalysis
Rasero-Almansa, Antonia M.,Iglesias, Marta,Sánchez, Félix
, p. 106790 - 106797 (2016/11/23)
Bimetallic Zr(Ti)-NDC based metal-organic frameworks (MOFs) have been prepared by incorporation of titanium(iv) into zirconium(iv)-NDC-MOFs (UiO family). The resulting materials maintain thermal (up to 500 °C), chemical and structural stability with respect to parent Zr-MOFs as can be deduced from XRD, N2 adsorption, FTIR and thermal analysis. The materials have been studied in Lewis acid catalyzed reactions, such as, domino Meerwein-Ponndorf-Verley (MPV) reduction-etherification of p-methoxybenzaldehyde with butanol, isomerization of α-pinene oxide and cyclization of citronellal.
Chemoselective formation of unsymmetrically substituted ethers from catalytic reductive coupling of aldehydes and ketones with alcohols in aqueous solution
Kalutharage, Nishantha,Yi, Chae S.
supporting information, p. 1778 - 1781 (2015/04/14)
A well-defined cationic Ru-H complex catalyzes reductive etherification of aldehydes and ketones with alcohols. The catalytic method employs environmentally benign water as the solvent and cheaply available molecular hydrogen as the reducing agent to afford unsymmetrical ethers in a highly chemoselective manner.
BiBr3, an efficient catalyst for the benzylation of alcohols: 2-Phenyl- 2-propyl, a new benzyl-type protecting group
Boyer, Bernard,Keramane, El-Mehdi,Roque, Jean-Pierre,Pavia, André A.
, p. 2891 - 2894 (2007/10/03)
The benzylation of aliphatic alcohols with various benzylic alcohols has been achieved in the presence of BiBr3 under mild conditions. 2- Phenylpropan-2-ol proved to be the most efficient and can be considered as a novel protecting group. (C) 2000 Elsevier Science Ltd.
Hypervalent (tert-butylperoxy)iodanes generate iodine-centered radicals at room temperature in solution: Oxidation and deprotection of benzyl and allyl ethers, and evidence for generation of α-oxy carbon radicals
Ochiai, Masahito,Ito, Takao,Takahashi, Hideo,Nakanishi, Akinobu,Toyonari, Mika,Sueda, Takuya,Goto, Satoru,Shiro, Motoo
, p. 7716 - 7730 (2007/10/03)
1-(tert-Butylperoxy)-1,2-benziodoxol-3(1H)-one (1a) oxidizes benzyl and allyl ethers to the esters at room temperature in benzene or cyclohexane in the presence of alkali metal carbonates. Since this reaction is compatible with other protecting groups such as MOM, THP, and TBDMS ethers, and acetoxy groups, and because esters are readily hydrolyzed under basic conditions, this new method provides a convenient and effective alternative to the usual reductive deprotection. Oxidation with 1a occurs readily with C-H bonds activated by both enthalpic effects (benzylic, allylic, and propargylic C-H bonds) and/or polar effects (α-oxy C-H bonds), generating α-oxy carbon-centered radicals, which can be detected by nitroxyl radical trapping. Measurement of the relative rates of oxidation for a series of ring-substituted benzyl n-butyl ethers 2d and 2p-s indicated that electron-releasing groups such as p-MeO and p-Me groups increase the rate of oxidation, and Hammett correlation of the relative rate factors with the σ+ constants of substituents afforded the reaction constant ρ+ = -0.30. The large value of the isotope effect obtained for the oxidation of benzyl n-butyl ether 2d (k(H)/k(D) = 12-14) indicates that the rate-determining step of the reactions probably involves a high degree of benzylic C-H bond breaking. The effects of molecular dioxygen were examined, and the mechanism involving the intermediacy of the tert-butylperoxy acetal 5 and/or the hydroperoxy acetal 32 is proposed. Particularly noteworthy is the finding that (tert-butylperoxy)iodane 1a can generate the tert-butylperoxy radical and the iodine-centered radical 33a, even at room temperature in solution, via homolytic bond cleavage of the hypervalent iodine(III)-peroxy bond.
The Reaction of Alkyllithium Reagents with Furan-3-carboxylic Acid. A Synthesis of 4-(Furan-3'-yl)-1-methylbutyltriphenylphosphonium Iodide
Dimitriadis, Eugene,Massy-Westropp, Ralph A.
, p. 619 - 627 (2007/10/02)
The ketones, 4-benzyloxy-1-(furan-3'-yl)pentan-1-one and 4-benzyloxy-1-(furan-3'-yl(butan-1-one, have been prepared by generating the required alkyllithium reagent in the presence of lithium furan-3-carboxylate.The latter ketone has been transformed to 4-(furan-3'-yl)-1-methylbutyltriphenylphosphonium iodide.
FLUORIDE SALTS ON ALUMINA AS REAGENTS FOR ALKYLATION OF PHENOLS AND ALCOHOLS.
ANDO,YAMAWAKI,KAWATE,SUMI,HANAFUSA
, p. 2504 - 2507 (2007/10/02)
THE EFFECTIVENESS OF ALKALI METAL FLUORIDES IMPREGNATED ON ALUMINA AS A REAGENT FOR PROMOTING ALKYLATION WAS OPTIMIZED WITH RESPECT TO THE METAL CATION, THE AMOUNT OF IMPREGNATION, AND THE REACTION SOLVENT. POTASSIUM OR CAESIUM FLUORIDE ONALUMINA IN ACETONITRILE OR 1,2-DIMETHOXYETHANE WAS CONCLUDED TO BE THE BEST REACTION SYSTEM FOR GENERAL USE. O-ALKYLATION OF SUBSTITUTED PHENOLS, PRIMARY AND SECONDARY ALCOHOLS, AND A GLYCOL WAS CARRIED OUT MOSTLY IN GOOD YIELDS UNDER MILDCONDITIONS WITH SIMPLE EXPERIMENTAL PROCEDURES.
Prins Reactions of Arylaldehydes, V: On the Reaction with 2-Butene and with Cyclohexene
Griengl, Herfried,Mayer, Arnulf,Geppert, Klaus Peter
, p. 1007 - 1016 (2007/10/02)
By reaction of 2--2-phenyl-1,3-dithiane (1a) with cis-2-butene oxide, subsequent reduction and acetalization c-4,t-5-dimethyl-r-2,c-6-diphenyl-1,3-dioxane (3a) and t-4,c-5-dimethyl-r-2,c-6-diphenyl-1,3-dioxane (3b) were synthesized as model compounds.For the same purpose by aldol reaction of cyclohexanone and reduction (1RS,2SR)-2cyclohexanol (7a), (1RS,2RS)-2cyclohexanol (8a), and (1RS,2RS)-2cyclohexanol (8b), and by acetalization (2α,4α,4aβ,8aβ)-2,4-bis(4-methoxyphenyl)hexahydro-4H-1,3-benzodioxin (9a) and (2α,4α,4aα,8aβ)-2,4-bis(4-nitrophenyl)hexahydro-4H-1,3-benzodioxin (10b) were obtained.From Prins reactions, starting with 2-butene 3a, c-4,c-5-dimethyl-r-2,c-6-diphenyl-1,3-dioxane (3c), r-4,t-5-dimethyl-c-6-phenyl-1,3,2-dioxathiane-2,2-dioxide (4), and (2Z,4E)-1,5-diphenyl-4-methyl-2,4-pentadien-1-on (5), and starting with cyclohexene (E)-3-(4-methoxybenzylidene)cyclohexenyl-4-methoxyphenyl ketone (11) have been isolated in low yields. - Keywords: Addition reactions; 1,3-Diols; 1,3-Dioxanes
