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

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11 引文 斯高帕斯(Scopus)

摘要

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.

原文英語
頁(從 - 到)10541-10551
頁數11
期刊Tetrahedron
61
發行號44
DOIs
出版狀態已發佈 - 2005 十月 31

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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