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Rearrangement of S-(2-aminoethyl) thiophosphates to N-(2-mercaptoethyl)- phosphoramidates

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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 calculations indicate that the reaction proceeds in a two step process when two explicit solvent molecules are included. In the presence of water the rearrangement reaction proceeds in competition with hydrolysis.

Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Pages (from-to)5826-5833
Number of pages8
Publication statusPublished - 1 Jan 2007
Externally publishedYes

    Research areas

  • Density functional theory, Hydrolysis, Phosphoramidate, Rearrangement, Thiophosphate

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