An Efficient One-Pot Synthesis of Oxime Ethers from Alcohols Using Triphenylphosphine/Carbon Tetrachloride

被引：16

作者：

Rad, Mohammad Navid Soltani ^{[1
]}

Khalafi-Nezhad, Ali ^{[2
]}

Karimitabar, Fatemeh ^{[2
]}

Behrouz, Somayeh ^{[1
]}

机构：

[1] Shiraz Univ Technol, Fac Basic Sci, Dept Chem, Shiraz 71555313, Iran

[2] Shiraz Univ, Dept Chem, Coll Sci, Shiraz 71454, Iran

来源：

SYNTHESIS-STUTTGART | 2010年 / 10期

关键词：

oxime; alcohol; O-alkylation; triphenylphosphine; carbon tetrachloride; DBU; TETRACHLOROMETHANE-POTASSIUM CARBONATE; ALLYLIC SUBSTITUTION; ASYMMETRIC-SYNTHESIS; MICHAEL ADDITION; RADICAL-ADDITION; ALKYLATION; DERIVATIVES; CONVERSION; ENVIROXIME; ARYL;

D O I：

10.1055/s-0029-1218711

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1724 / 1730

页数：7

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