75949-06-3Relevant articles and documents
Reductive Etherification via Anion-Binding Catalysis
Zhao, Chenfei,Sojdak, Christopher A.,Myint, Wazo,Seidel, Daniel
supporting information, p. 10224 - 10227 (2017/08/10)
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.
Direct conversion of tosylhydrazones to tert-butyl ethers under Bamford-Stevens reaction conditions
Chandrasekhar,Rajaiah,Chandraiah,Narsimha Swamy
, p. 1779 - 1780 (2007/10/03)
A new method for the preparation of tert-butyl ethers is described starting from aryl aldehyde and ketone tosylhydrazones under Bamford-Stevens reaction conditions (t-BuOK/t-BuOH).
Photochemistry of phosphate esters: An efficient method for the generation of electrophiles
Givens, Richard S.,Matuszewski, Bogdan,Athey, Phillip S.,Robert Stoner
, p. 6016 - 6021 (2007/10/02)
The photochemical cleavage of benzyl diethyl phosphates, 1a-g, has been examined in tert-butyl alcohol, which produces the corresponding benzyl tert-butyl ether as the major solvolysis product upon direct irradiation. The multiplicity of the reactive excited state has been established as the singlet state. Evidence favoring an intermediate benzyl cation-phosphate ion pair formed from photofragmentation includes oxygen-18 scrambling, racemization of chiral benzyl phosphates, and substituent effects on the rate of reaction. The existence of an electrophilic intermediate is further supported by a linear free energy relationship for the rate of disappearance of 1, kdis, with Hammett σ, which gave a ρ value of -0.90 and for the rate of appearance of 2, kapp, a Hammett ρ value of -0.97. Possible mechanisms including an electron transfer either before or after homolysis or simple heterolysis of the ester bond are evaluated.