Synthesis p. 1724 - 1730 (2010)
Update date:2022-09-26
Topics:
Soltani Rad, Mohammad Navid
Khalafi-Nezhad, Ali
Karimitabar, Fatemeh
Behrouz, Somayeh
A convenient and efficient one-pot O-alkylation of oximes from alcohols 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 catalytic amounts of tetrabutylammonium iodide in refluxing acetonitrile regioselectively furnishes the corresponding O-alkyl ethers in good yields. This methodology is highly efficient O-alkylation of oximes with various structurally diverse alcohols. Semiempirical quantum-mechanic calculations (AM1) for unsymmetrical oxime ethers, indicated a lower heat of formation for Z-isomers. Georg Thieme Verlag Stuttgart - New York.
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Doi:10.1021/ma100814v
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