Reduction of acetals with samarium diiodide in acetonitrile in the presence of Lewis acids.
Transformation of acetals into ethers by partial reduction using a samarium diiodide-Lewis acids-acetonitrile system is described. The reaction with aromatic acetals occurred in good yields in the presence of aluminum chloride (2 eq) whereas the corresponding aliphatic, vinylic, and alkynyl derivatives did not afford ethers under the same conditions. Beta-elimination to give an enol ether becomes predominant when aliphatic acetals that possess a hydrogen at the 2-position are treated with iodotrimethylsilane in the presence of SmI2 or SmI3.
Kunishima
M
M
Faculty of Pharmaceutical Sciences and High Technology Research Center, Kobe Gakuin University, Japan. kunisima@kgu-p.pharm.kobegakuin.ac.jp
Nakata
D
D
Sakuma
T
T
Kono
K
K
Sato
S
S
Tani
S
S
D000080:Acetals / Q000737:chemistry*; D000097:Acetonitriles / Q000737:chemistry*; D000143:Acids / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D010084:Oxidation-Reduction; D012493:Samarium / Q000737:chemistry*; D013057:Spectrum Analysis
D000080:Acetals; D000097:Acetonitriles; D000143:Acids; D007454:Iodides; D012493:Samarium; C409809:samarium diiodide; C032159:acetonitrile