Tetrahedron letters

Novel method of deoxidation of alcohols and its use in synthesis of covalent perchlorates

NS Zefirov, VV Zhdankin, VD Sorokin, AS Koz'min

Index: Zefirov, Nikolai S.; Zhdankin, Viktor V.; Sorokin, Viktor D.; Koz'min, Anatoly S. Tetrahedron Letters, 1985 , vol. 26, # 50 p. 6243 - 6244

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Citation Number: 2

Abstract

Analogous mechanism intermediacy of chlorosulfonium salt of type 6 has been suggested for chlorinolysis of alkyl arylsylfenates in AcOH (Ref 7b). We have shown that this reaction in the presence of lithium perchlorate gives covalent perchlorates. For instance, -2-chlorocyclohexyl 2,4-dinitrophenylsulfenate reacts with chlorine in AcOEt in the presence of 5 mol-eqv of lithium perchlorate to give 2-chlorocyclohexyl perchlorates 2 (40% yield) and 3 (27% yield).