101746-67-2Relevant academic research and scientific papers
Nickel-catalyzed direct synthesis of dialkoxymethane ethers
Subaramanian, Murugan,Bera, Abhijit,Prasad, Bhagavatula L V,Balaraman, Ekambaram
, p. 1153 - 1159 (2017)
221A simple and efficient method for the preparation of dialkoxymethane ethers (oxymethylene ethers) from alcohols and paraformaldehyde in the presence of commercially available nickel(II) salt is described. The reaction proceeds readily under neutral, solvent-free conditions using paraformaldehyde as a C 1 source. The present strategy has a broad substrate scope including aliphatic (both primary and secondary) and aromatic alcohols and provides a benign method for the preparation of symmetrical dialkoxymethanes in good yields (up to 89%). Graphical Abstract: SYNOPSIS A facile nickel-catalyzed synthesis of dialkoxymethane ethers from alcohols and paraformaldehyde using inexpensive, commercially available NiBr 2 is reported. The reaction proceeds readily under mild, neutral and solvent-free conditions. [Figure not available: see fulltext.].
Dimethyl sulfoxide as a "methylene" source: Ru(ii) photo-catalysed facile synthesis of acetals from alcohols
Talukdar, Ranadeep
supporting information, p. 13334 - 13338 (2019/09/06)
Acetals are important molecules with versatile reactivity and uses. For the first time a simple photo-catalysed facile synthesis of formaldehyde acetals is documented herein upon the reaction of alcohols with dimethyl sulfoxide under very mild conditions in the presence of air. The reactions require only 1 mol% of RuII(bpy)3Cl2 photocatalyst under blue LED irradiation (λ = 445 nm) to give good to excellent yields of the corresponding acetal products. Here DMSO acts as a "methylene" source.
A new and more efficient synthesis of methylene acetals
Chu, Guobiao,Zhang, Yanqiao,Li, Chunbao,Zhang, Yuqing
experimental part, p. 3828 - 3832 (2010/03/03)
A new and efficient synthesis of benzyl chlorides and methylene acetals by use of 2,4-dichloro-6-methoxy[l,3,5]triazine (MeOTCT) and dimethyl sulfoxide has been developed. Chlorides are the major products for benzyl alcohols, while methylene acetals are the major products for secondary alcohols. This procedure provides the highest yields so far for methylene acetals of steroids. A plausible mechanism is proposed on the basis of the experiments. Georg Thieme Verlag Stuttgart.
Efficient and selective formation of mixed acetals by Nafion-H SAC-13 silica nanocomposite solid acid catalyst
Ledneczki, Istvan,Molnar, Arpad
, p. 3683 - 3690 (2007/10/03)
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.
Acid catalysis vs. electron-transfer catalysis via organic cations or cation-radicals as the reactive intermediate. Are these distinctive mechanisms?
Rathore, Rajendra,Kochi, Jay K.
, p. 114 - 130 (2007/10/03)
Proton transfer to aromatic and olefinic donors (D) leads to the facile interchange of transient carbocations (DH+) and cation-radical (D+.). The same types of cation and cation-radical are reactive intermediates in the acid catalysis and the electron-transfer catalysis of such organic transformations as benzylic coupling, epoxide/pinacol rearrangements and cis-trans isomerization of stilbenes when they are both carried out under otherwise identical reaction conditions. However, the rapid exchange of diamagnetic cations and paramagnetic cation-radicals blurs the traditional view of separate electrophilic and homolytic processes, and rigorous experimental evidence is required to establish whether acid catalysis and electron-transfer catalysis actually represent distinct mechanistic categories. Acta Chemica Scandinavica 1998.
Radical-Cation Catalysis in the Synthesis of Diphenylmethanes via the Dealkylative Coupling of Benzylic Ethers
Rathore, Rajendra,Kochi, Jay K.
, p. 7479 - 7490 (2007/10/03)
The dealkylative coupling of benzyl alkyl ethers (ArCH2OR) to yield the corresponding diarylmethanes (ArCH2Ar) together with dialkoxymethane (ROCH2OR) is catalyzed by small amounts of 1-electron oxidants (such as aromatic cation radicals, NO(1+), etc.) or by an equivalent electrochemical (anodic) method.The catalytic method is successfully employed for the facile synthesis of a novel macrocyclic crown ether 18 that contains a diarylmethane linkage.On the basis of the spectral observation of the radical cation ArCH2OR.+ and the excellent catalytic efficiency with turnover numbers in excess of 1E2, an electron-transfer and an alternative electrophilic chain mechanism are discussed for the dealkylative coupling process.
A One-Step Conversion of p-Methoxybenzyl Ethers into Methoxymethyl Ethers by the Action of Dimethoxymethane in the Presence of Tin(II) Bromide and Bromomethyl Methyl Ether
Oriyama, Takeshi,Kimura, Mikio,Koga, Gen
, p. 885 - 887 (2007/10/02)
The combined use of dimethoxymethane with catalytic amounts of tin(II) bromide and bromomethyl methyl ether cleaves p-methoxybenzyl ethers to give methoxymethyl ethers in good yields.The chemoselective conversion of p-methoxybenzyl ethers in the presence of the benzyl ether function into methoxymethyl ethers has also occurred successfully.
