54354-04-0Relevant articles and documents
BiCl3-Facilitated removal of methoxymethyl-ether/ester derivatives and DFT study of -O-C-O- bond cleavage
Pacherille, Angela,Tuga, Beza,Hallooman, Dhanashree,Dos Reis, Isaac,Vermette, Mélodie,Issack, Bilkiss B.,Rhyman, Lydia,Ramasami, Ponnadurai,Sunasee, Rajesh
supporting information, p. 7109 - 7116 (2021/05/03)
A simple method for the cleavage of methoxymethyl (MOM)-ether and ester derivatives using bismuth trichloride (BiCl3) is described. The alkyl, alkenyl, alkynyl, benzyl and anthracene MOM ether derivatives, as well as MOM esters of both aliphatic and aromatic carboxylic acids, were deprotected in good yields. To better understand the molecular roles of BiCl3and water for MOM cleavage, two possible binding pathways were investigated using the density functional theory (DFT) method. The theoretical results indicate the differential initial binding site preferences of phenolic and alcoholic MOM substrates to the Bi atom and suggest that water plays a key role in facilitating the cleavage of the MOM group.
Synthesis of alpha-halo ethers from symmetric acetals and in situ methoxymethylation of an alcohol [1-methoxymethoxy-1-phenylethane]
Berliner, Martin,Belecki, Katherine,Paquette, William D.,Wipf, Peter
, p. 102 - 110 (2017/09/16)
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Anodic Oxidation of O-Benzoylated α-Hydroxyacetic Acids Concerning the Structure of the Cationic Intermediate
Thomas, H. Guenter,Kessel, Stephan,Mueller, Edwin
, p. 2173 - 2177 (2007/10/02)
Anodic oxidation of (benzoyloxy)acetic acid (1b) at graphite electrodes in methanol leads to the substitution product methoxymethyl benzoate (3) as well as the fragmentation product methyl benzoate (4) recovering all labeled oxygen in the carbonyl groups.This result proves that the 1,3-dioxetanylium ion 2' is not involving in the non-Kolbe electrolysis of O-benzoylated α-hydroxyacetic acids.The cationic intermediate 2 is of open-chain structure.