6795-87-5Relevant articles and documents
Alcohol Dehydration: Mechanism of Ether Formation Using an Alumina Catalyst
Shi, Buchang,Davis, Burtron H.
, p. 359 - 367 (2007/10/03)
Ether formation during the dehydration of secondary alcohols, namely, 2-butanol, 3-pentanol, and 1-cyclopentylethanol, was investigated.Using the proper reaction conditions, the yield of di-2-butyl ether during the dehydration of 2-butanol on alumina can be as high as 40percent.That ether is formed by adding an alcohol to the alkene is ruled out by the results from deuterium tracer studies.Results from experiments using S(+)-2-butanol suggest that the formation of di-2-butyl ether occurs by a SN2-type mechanism.
Onium Ylide Chemistry. 3. Evidence for Competing Oxonium Ylide Formation with C-H Insertion in Meerwein's Reaction of Methylene and Methylene-d2 with Dialkyl Ethers
Olah, George A.,Doggweiler, Hans,Felberg, Jeff D.
, p. 2116 - 2120 (2007/10/02)
Meerwein's reaction of singlet methylene, produced by photolysis of diazomethane, with dialkyl ethers has been reinvestigated on the basis of reactions using CD2N2.In competition with methylene insertion into the various C-H bonds, about 10percent of methyl alkyl ether and small amounts of dimethyl ether formation are also observed.This indicates evidence for competing attack of methylene on oxygen leading to the corresponding intermediate methylenedialkyloxonium ylides which are immediately protonated by methyl alkohol (or water)impurity present in the reaction medium togive the corresponding methyldialkyloxonium ions.Dealkylative cleavage of the latter gives the observed methyl alkyl ethers.By the use of deuterium-labeled diazomethane CD2N2 it has been shown that ethylene and propylene formed under the reaction conditions are coming predominantly from diazomethane itself and not via intramolecular β-elimination of the oxonium ylides.