A Novel Synthetic Method for Crown Ethers by a Redox Reaction Utilizing the Intermediate from Diphenyldiazomethane and 2,3-Dichloro-5,6-dicyanobenzoquinone
A synthetic method for the new crown ethers possessing a diphenylmethylene moiety by the reaction of diphenyldiazomethane (DDM) and 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) under the influence of oligoethylene glycols is described.The two types of crown ethers with 1:1 and 2:2 composition of diphenylmethylene/oligoethylene glycol moiety were obtained together with the noncyclic 1:2 compositional diols.The product distributions were dependent on the relative quantities and the manner of addition of the oligoethylene glycols.
FACILE SYNTHETIC METHODS OF ACETALS AND CROWN ETHERS FROM THE REACTION OF DIPHENYLDIAZOMETHANE WITH 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE IN THE PRESENCE OF ALCOHOLS
The reaction of diphenyldiazomethane with 2,3-dichloro-5,6-dicyanobenzoquinone in the presence of alcohols and thiols gave the corresponding benzophenone acetals and thioacetals at 20-25 deg C in 1,2-dichloroethane.The mechanism of the reaction will be discussed.
Oshima, Takumi,Nishioka, Ryoji,Nagai, Toshikazu
p. 3919 - 3922
(2007/10/02)
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