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

doi:10.1016/j.tet.2005.08.041

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^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

13 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 language	English
Pages (from-to)	10541-10551
Number of pages	11
Journal	Tetrahedron
Volume	61
Issue number	44
DOIs	https://doi.org/10.1016/j.tet.2005.08.041
Publication status	Published - 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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title = "The study of reaction mechanism for the transformation of nitronate into nitrile by phosphorus trichloride",

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.",

keywords = "Cyclic compounds, Malonate ester, Nitrile, Nitrile oxide intermediate, PCl, Reaction mechanism, β-Nitrostyrene",

author = "Zhijay Tu and Yaochung Jang and Chunchi Lin and Liu, {Ju Tsung} and Jianming Hsu and Sastry, {M. N.V.} and Yao, {Ching Fa}",

note = "Funding Information: Financial support of this work was provided by the National Science Council of the Republic of China and National Taiwan Normal University (ORD93-C) is gratefully acknowledged. ",

year = "2005",

month = oct,

day = "31",

doi = "10.1016/j.tet.2005.08.041",

language = "English",

volume = "61",

pages = "10541--10551",

journal = "Tetrahedron",

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publisher = "Elsevier Limited",

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TY - JOUR

T1 - The study of reaction mechanism for the transformation of nitronate into nitrile by phosphorus trichloride

AU - Tu, Zhijay

AU - Jang, Yaochung

AU - Lin, Chunchi

AU - Liu, Ju Tsung

AU - Hsu, Jianming

AU - Sastry, M. N.V.

AU - Yao, Ching Fa

N1 - Funding Information: Financial support of this work was provided by the National Science Council of the Republic of China and National Taiwan Normal University (ORD93-C) is gratefully acknowledged.

PY - 2005/10/31

Y1 - 2005/10/31

N2 - 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.

AB - 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.

KW - Cyclic compounds

KW - Malonate ester

KW - Nitrile

KW - Nitrile oxide intermediate

KW - PCl

KW - Reaction mechanism

KW - β-Nitrostyrene

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U2 - 10.1016/j.tet.2005.08.041

DO - 10.1016/j.tet.2005.08.041

M3 - Article

AN - SCOPUS:25844450975

SN - 0040-4020

VL - 61

SP - 10541

EP - 10551

JO - Tetrahedron

JF - Tetrahedron

IS - 44

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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