- P4VPy–CuO nanoparticles as a novel and reusable catalyst: application at the protection of alcohols, phenols and amines
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P4VPy–CuO nanoparticles were synthesized using ultrasound irradiations. Relevant properties of the synthesized nanoparticles were investigated by X-ray diffraction, scanning electron microscopy, transmission electron microscopy and Fourier transform infrared spectroscopy. After identification, the prepared reagent was used for the promotion of different types of protection reactions of alcohols, phenols and amines. Easy workup, short reaction times, excellent yields, relatively low cost and reusability of the catalyst are the striking features of the reported methods.
- Shirini, Farhad,Fallah-Shojaei, Abdollah,Abedini, Masoumeh,Samavi, Laleh
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p. 1699 - 1712
(2016/07/27)
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- H3PW12O40at the[bmim][FeCl4]: A green catalytic system for alkoxymethylation of alcohols and their one-pot interconversion to acetates and TMS-ethers
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12-Tungstophosphoric acid immobilized on [bmim][FeCl4] was found to be an efficient catalyst for chemoselective methoxymethylation and ethxoymethylation of alcohols and also one-pot conversion of MOM- or EOM-ethers to their corresponding acetates and TMS-ethers under thermal conditions and microwave irradiation. These procedures were simple, rapid and the corresponding products were obtained in high yields. The catalyst exhibited remarkable reactivity and was reusable.
- Mohammadpoor-Baltork,Moghadam,Tangestaninejad,Mirkhani,Khosropour,Mirjafari
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experimental part
p. 513 - 524
(2012/06/16)
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- [InCl4]: An efficient catalyst-medium for alkoxymethylation of alcohols and their interconversion to acetates and TMS-ethers
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A simple, green and chemoselective method for methoxymethylation and ethoxymethylation of primary and secondary alcohols using a Lewis acidic room temperature ionic liquid, [C4mim][InCl4], as catalyst and reaction medium under ambient temperature, microwave and ultrasonic irradiations is reported. In this catalytic system, the corresponding MOM-and EOM-ethers are obtained in excellent yields and in short reaction times. Furthermore, this catalytic system was used for mild and efficient transformations of these protected alcohols to their corresponding acetates and trimethylsilyl ethers under thermal conditions and microwave and ultrasonic irradiations.
- Mohammadpoor-Baltork, Iraj,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Khosropour, Ahmad Reza,Mirjafari, Arsalan
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experimental part
p. 568 - 579
(2012/05/05)
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- A facile method for the rapid and selective deprotection of methoxymethyl (MOM) ethers
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We describe a rapid and efficient method for selective deprotection of methoxymethyl (MOM) ethers using ZnBr2 and n-PrSH, which completely removed MOM from diverse MOM ethers of primary, secondary, and tertiary alcohols or phenol derivatives. The deprotection takes less than ten minutes with both high yield and selectivity in the presence of other protecting groups. In addition, the rapid deprotection of MOM ethers of tertiary hydroxyls in high yield with no epimerization allows MOM to be a suitable protecting group for tertiary alcohols.
- Han, Jae Hyun,Kwon, Young Eun,Sohn, Jeong-Hun,Ryu, Do Hyun
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experimental part
p. 1673 - 1677
(2010/04/04)
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- Highly efficient and selective methoxymethylation of alcohols and phenols catalyzed by reusable ZrO(OTf)2 under solvent-free conditions
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Different primary, secondary, and tertiary alcohols were efficiently converted to their corresponding methoxymethyl ethers with formaldehyde dimethyl acetal in the presence of catalytic amounts of ZrO(OTf)2 at room temperature. Phenols were als
- Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj,Khajehzadeh, Mostafa
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experimental part
p. 641 - 647
(2011/05/04)
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- High-valent [SnIV(Br8TPP)(OTf)2] as a highly efficient and reusable catalyst for selective methoxymethylation of alcohols and phenols: The effect of substituted bromines on the catalytic activity
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High-valent tin(IV)octabromotetraphenylporphyrinato trifluoromethanesulfonate, [SnIV(Br8TPP)(OTf)2], was used for selective methoxymethylation of alcohols and phenols with formaldehyde dimethyl acetal (FDMA) at room temper
- Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj,Khajehzadeh, Mostafa,Kosari, Farshid,Araghi, Mehdi
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experimental part
p. 238 - 243
(2010/04/04)
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- Highly efficient and selective methoxymethylation of alcohols and phenols catalyzed by high-valent tin(IV) porphyrin
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An efficient and selective method for methoxymethylation of alcohols and phenols with formaldehyde dimethyl acetal (FDMA) catalyzed by electron deficient tin(IV)tetraphenylporphyrinato trifluoromethanesulfonate, [SnIV(TPP)(OTf)2], is
- Gharaati, Shadab,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj,Kosari, Farshid
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experimental part
p. 1995 - 2000
(2011/01/07)
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- A mild and efficient method for the methoxymethylation and acetylation of alcohols promoted by benzyltriphenylphosphonium tribromide
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A mild and efficient method for the conversion of alcohols to their corresponding methoxymethyl ethers and acetates using benzyltriphenylphosphonium tribromide (BTPTB) as catalyst is described. All reactions were performed under completely heterogeneous reaction conditions in good to high yields.
- Shirini, Farhad,Imanzadeh, Gholam Hossein,Mousazadeh, Seyyed Ali Reza,Mohammadpoor-Baltork, Iraj,Abedin, Masoumeh
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experimental part
p. 1187 - 1190
(2011/10/05)
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- Melamine trisulfonic acid (MTSA): A new efficient catalyst for the chemoselective methoxymethylation of alcohols
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Melamine trisulfonic acid, which is easily prepared by the reaction of melamine with neat chlorosulfonic acid, is able to efficiently catalyze the chemoselective methoxymethylation of alcohols with dimethoxymethane (DMM). All reactions were performed unde
- Shirini, Farhad,Zolfigol, Mohammad Ali,Albadi, Jalal
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experimental part
p. 910 - 914
(2010/05/01)
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- Synthesis of dialkyl ethers from organotrifluoroborates and acetals
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(Chemical Equation Presented) The formation of ethers by C-O bond formation under harsh basic or acidic conditions is an entrenched synthetic disconnection in organic chemistry. We report a strategic alternative that involves the BF3?OEt2
- Mitchell, T. Andrew,Bode, Jeffrey W.
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supporting information; experimental part
p. 18057 - 18059
(2010/03/26)
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- H3PW12O40 - A selective, environmentally benign, and reusable catalyst for the preparation of methoxymethyl and ethoxymethyl ethers and their deprotections under mild conditions
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Different types of primary and secondary alcohols were efficiently transformed to their corresponding methoxymethyl (MOM) and ethoxymethyl (EOM) ethers in the presence of catalytic amounts of H3PW 12O40 at room temperature under solvent-free conditions. Selective protection of primary and secondary alcohols in the presence of phenols and tertiary alcohols was achieved by this method. Deprotection of these ethers to their parent alcohols was also performed using this catalyst in ethanol under reflux conditions. We have also found that primary and secondary MOM- and EOM-ethers are selectively deprotected in the presence of phenolic and tertiary ones, methyl and benzyl ethers, esters, and trimethylsilyl ethers by this catalyst. The notable advantages of this protocol are high yields, short reaction times, easy work-up, non-toxicity, easy availability and handling, eco-friendly, and reusability of the catalyst.
- Mohammadpoor-Baltork, Iraj,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mirjafari, Arsalan
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p. 831 - 840
(2008/12/21)
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- Metal hydrogen sulfates catalyzed methoxymethylation of alcohols under solvent-free conditions
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Methoxymethylation of a variety of alcohols was performed by using formaldehyde dimethoxy acetal in the presence of metal hydrogen sulfate M(HSO4)n at room temperature and solvent-free conditions. The methoxymethyl ethers (MOM-ethers
- Niknam, Khodabakhsh,Zolfigol, Mohammad Ali,Shayegh, Mohsen,Zare, Reza
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p. 1067 - 1073
(2008/02/13)
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- HYDROXY-PROTECTING REAGENT AND METHOD OF PROTECTING HYDROXY WITH THE SAME
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The present invention relates to a method of protecting a hydroxyl group, which includes reacting a hydroxyl group-containing compound with a compound represented by the formula (I) : wherein R is a phenyl group optionally having substituent(s), an alkyl
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Page/Page column 10-11
(2008/06/13)
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- Simple, rapid procedure for the synthesis of chloromethyl methyl ether and other chloro alkyl ethers
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Zinc(II) salts catalyze the reaction between acetals and acid halides to provide haloalkyl ethers in near-quantitative yield. Reactions from millimole to mole scale are typically complete in 1-4 h with 0.01 mol % catalyst. The solutions of haloalkyl ethers thus obtained can be utilized directly in reactions in which the presence of the ester byproduct does not interfere. Excess haloalkyl ether is destroyed on workup, thereby minimizing exposure to this class of carcinogenic compounds.
- Berliner, Martin A.,Belecki, Katherine
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p. 9618 - 9621
(2007/10/03)
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- Molybdatophosphoric acid as a catalyst for the methoxymethylation of alcohols under solvent-free conditions
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The methoxymethylation of alcohols was performed using formaldehyde dimethoxy acetal in the presence of H3PMo12O 40·xH2O at room temperature under solvent-free conditions.
- Zolfigol, Mohammad Ali,Shiri, Morteza
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p. 165 - 166
(2007/10/03)
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- Efficient and selective formation of mixed acetals by Nafion-H SAC-13 silica nanocomposite solid acid catalyst
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Various types of hydroxy compounds can readily be converted to the corresponding mixed acetals with dialkoxymethanes in the presence of SAC-13 solid superacid. The transformation is almost instantaneous, product acetals are isolated in good to excellent yields, and the catalyst can be reused with minor loss of activity. Comparative studies were also carried out with p-toluenesulfonic acid and BF3·OEt2.
- Ledneczki, Istvan,Molnar, Arpad
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p. 3683 - 3690
(2007/10/03)
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- New efficient method of alkoxymethyl etherification of secondary alcohols
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A new efficient method of MOM etherification of secondary alcohols using 2-(chloromethyl)-3,5-dioxahex-1-ene (Okahara's reagent) is reported.
- Watanabe, Yosuke,Ikemoto, Tetsuya
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p. 5795 - 5797
(2007/10/03)
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