Stereochemistry and Reactions of Aziridinyl-phosphinothionates Derived from Amino Acids

Akinori Hirashima, Morifusa Eto

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)


Aziridinylphosphinothionates were prepared from optically active ethyl hydrogen phenylphos-phonothionates and l-bromo-2-alkanamines derived from leucine or valine. The aziridine ring was opened by the action of some nucleophiles. Refluxing the aziridinylphosphinothionates in acetone with sodium iodide caused hydrolysis accompanied by the rearrangement of the sulfur atom to give β-mercaptoethylphosphonamidates. The reaction mechanism was discussed with stereochemical considerations. The insecticidal activity of the products was also examined.

Original languageEnglish
Pages (from-to)829-838
Number of pages10
JournalAgricultural and Biological Chemistry
Issue number4
Publication statusPublished - Jan 1983
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • General Biochemistry,Genetics and Molecular Biology
  • General Agricultural and Biological Sciences


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