THE DEALKYLATION OF PHOSPHATE AND PHOSPHONATE ESTERS BY IODOTRIMETHYLSILANE - A MILD AND SELECTIVE PROCEDURE
THE DEALKYLATION OF PHOSPHATE AND PHOSPHONATE ESTERS BY IODOTRIMETHYLSILANE - A MILD AND SELECTIVE PROCEDURE
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DOI：
10.1039/p19800001150
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发表时间：
1980-01-01
期刊：
影响因子：
--
通讯作者：
INGLESON, D
中科院分区：
文献类型：
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作者：
BLACKBURN, GM;INGLESON, D
碘代三甲基硅烷将磷含氧酸的烷基酯转化为其相应的三甲基甲硅烷基酯和烷基碘。该反应在室温下快速且定量。在用于酯交换的条件下，该试剂对芳基磷酸酯官能团或对烷基羧酸酯、醚、溴烷、乙烯基和乙炔基官能团没有影响。三甲基甲硅烷基酯可通过蒸馏分离或溶剂解，无需使用甲醇或水纯化，得到脱烷基化的磷酸酯和膦酸酯物质。仅使用一当量的试剂无法实现膦酸二烷基酯的选择性单脱烷基化，这会导致混合产物的形成。
Iodotrimethylsilane transforms alkyl esters of phosphorus oxyacids into their corresponding trimethylsilyl esters and alkyl iodide. The reaction is rapid and quantitative at room temperature. The reagent has no effect on aryl phosphate ester functions or upon alkyl carboxylate, ether, bromoalkane, vinyl, and ethynyl functions under the conditions employed for transesterification. The trimethylsilyl esters can be isolated by distillation or solvolysed without purification using methanol or water to afford dealkylated phosphate and phosphonate species. Selective monodealkylation of dialkyl phosphonates cannot be achieved using only one equivalent of the reagent, which leads to the formation of mixed products.