Abstract
A convenient and efficient one-pot O-alkylation of oximes fromalcohols using triphenylphosphine in carbon tetrachloride is described.In this method, treatment of alcohols with a mixture of triphenylphosphine,carbon tetrachloride, oxime, and DBU in the presence of catalyticamounts of tetrabutylammonium iodide in refluxing acetonitrile regioselectivelyfurnishes the corresponding O-alkyl ethersin good yields. This methodology is highly efficient O-alkylationof oximes with various structurally diverse alcohols. Semiempiricalquantum-mechanic calculations (AM1) for unsymmetrical oxime ethers,indicated a lower heat of formation for Z-isomers.
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