Rearrangement of S??(2??Aminoethyl) Thiophosphates to N??(2??Mercaptoethyl) phosphoramidates
M Chen, A Maetzke, SJ Knak Jensen…
Index: Chen, Menglin; Maetzke, Alice; Knak Jensen, Svend J.; Gothelf, Kurt V. European Journal of Organic Chemistry, 2007 , # 35 p. 5826 - 5833
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Abstract
Abstract A novel rearrangement of S-(2-aminoethyl) thiophosphates to N-(2-mercaptoethyl) phosphoramidates was discovered and developed. The reaction proceeds smoothly at room temperature under basic conditions and the resulting thiol could subsequently be alkylated. The reaction mechanism is investigated by electron structure calculations using density functional theory at the B3LYP/6-31G (d) and B3LYP/6-311+ G (d, p) levels. The ...
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