Stereochemistry of cyclic ether formation—II : Intramolecular cyclisation of secondary aliphatic alcohols to tetrahydrofuran-type ethers |
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Authors: | MLj Mihailovi? S Gojkovi? S Konstantinovi? |
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Institution: | Department of Chemistry, Faculty of Sciences, University of Belgrade, Yugoslavia;Institute for Chemistry, Technology and Metallurgy, Belgrade, Yugoslavia |
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Abstract: | The mechanism and stereochemistry of δ-C atom functionalisation in the reactions of secondary straight-chain aliphatic alcohols with lead tetraacetate, ceric ammonium nitrate, and heavy metal (Pb4+, Hg2+, Ag+) salts (AcO)?1, O2?, CO32?-halogen (I2, Br2, Cl2) combinations are discussed. By demonstrating the intermediacy of 5-bromo-2-hexanol, it was confirmed that the dark silver oxidebromine induced cyclisation of 2-hexanol (and alcohols in general) involves (as the other hypohalite reactions) intramolecular 1,5-hydrogen abstraction by alkoxy radicals and formation of δ-bromohydrins. A novel and simple procedure for obtaining tetrahydrofurans from alcohols by way of the hypochlorite reaction, using silver or mercuric salts and chlorine, is described. |
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Keywords: | Address for correspondence: Department of Chemistry Faculty of Sciences Studentski trg 16 P O Box 550 11001 Belgrade Yugoslavia |
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