Dealkylation reaction of acetals, phosphonate, and phosphate esters with chlorotrimethylsilane/metal halide reagent in acetonitrile, and its application to the synthesis …

T Morita, Y Okamoto, H Sakurai

Index: Morita, Tsuyoshi; Okamoto, Yoshiki; Sakurai, Hiroshi Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 1 p. 267 - 273

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Citation Number: 39

Abstract

A mild and efficient method has been developed for carbon-oxygen bond cleavage using chlorotrimethylsilane/sodium iodide in acetonitrile. It was applied to synthetic transformation under nonaqueous and neutral conditions, such as acetal deprotection and the synthesis of phosphonic acids from the corresponding dialkyl phosphonates via methanolysis of their silyl esters. Effectiveness of various kinds of metal or ammonium iodides for this type of ...