The study of reaction mechanism for the transformation of nitronate into nitrile by phosphorus trichloride

Zhijay Tu, Yaochung Jang, Chunchi Lin, Ju Tsung Liu, Jianming Hsu, M. N.V. Sastry, Ching Fa Yao

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Nitronate was generated using β-nitrostyrene and the anion of dimethyl malonate in THF at 0°C. Subsequent treatment with PCl3 in the presence/absence of DMAP either in THF or pyridine afforded nitroalkane, chloroxime, and nitrile. Pyridine, THF, and THF-pyridine co-solvent as solvents were investigated under different conditions. With different anions of malonates containing dipolarphiles, cyclic compounds were obtained as major products indicating nitrile oxides were generated during the reaction. Based on the results, compared to that of the one reported in literature, a plausible mechanism involving nitrile oxide intermediate was proposed.

Original languageEnglish
Pages (from-to)10541-10551
Number of pages11
JournalTetrahedron
Volume61
Issue number44
DOIs
Publication statusPublished - 2005 Oct 31

Keywords

  • Cyclic compounds
  • Malonate ester
  • Nitrile
  • Nitrile oxide intermediate
  • PCl
  • Reaction mechanism
  • β-Nitrostyrene

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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