Isomerization of Halogenated Cyclopentene over a NH4F Catalyst

Chengping Zhang; Ruzhu Hu; Feiyao Qing; Hengdao Quan

doi:10.1002/cctc.201600055

Isomerization of Halogenated Cyclopentene over a NH₄F Catalyst

Chengping Zhang, Ruzhu Hu, Feiyao Qing, Hengdao Quan^*

^*Corresponding author for this work

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

3 Citations (Scopus)

Abstract

The mechanism of the halogen-transfer isomerization of halogenated cyclopentene was investigated over a NH₄F catalyst in DMF. This catalytic system was to have the unique ability to isomerize halogenated cyclopentene selectively. The process of migration of the F atom in the 3-position on the C(sp³) atom to the 4-position on the C(sp³) atom is in chemical equilibrium, whereas the process of migration of the F atom in the 2-position on the C(sp²) atom to the 3-position on the C(sp³) atom is not. Therefore, halogenated cyclopentene containing fluorine on either the C(sp³) or C(sp²) atom could be prepared selectively in terms of the NH₄F catalyst.

Original language	English
Pages (from-to)	1474-1478
Number of pages	5
Journal	ChemCatChem
Volume	8
Issue number	8
DOIs	https://doi.org/10.1002/cctc.201600055
Publication status	Published - 20 Apr 2016
Externally published	Yes

Keywords

halogen transfer
halogenated building block
halogenated cyclopentene
isomerization
reaction mechanisms

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10.1002/cctc.201600055

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title = "Isomerization of Halogenated Cyclopentene over a NH4F Catalyst",

abstract = "The mechanism of the halogen-transfer isomerization of halogenated cyclopentene was investigated over a NH4F catalyst in DMF. This catalytic system was to have the unique ability to isomerize halogenated cyclopentene selectively. The process of migration of the F atom in the 3-position on the C(sp3) atom to the 4-position on the C(sp3) atom is in chemical equilibrium, whereas the process of migration of the F atom in the 2-position on the C(sp2) atom to the 3-position on the C(sp3) atom is not. Therefore, halogenated cyclopentene containing fluorine on either the C(sp3) or C(sp2) atom could be prepared selectively in terms of the NH4F catalyst.",

keywords = "halogen transfer, halogenated building block, halogenated cyclopentene, isomerization, reaction mechanisms",

author = "Chengping Zhang and Ruzhu Hu and Feiyao Qing and Hengdao Quan",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

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TY - JOUR

T1 - Isomerization of Halogenated Cyclopentene over a NH4F Catalyst

AU - Zhang, Chengping

AU - Hu, Ruzhu

AU - Qing, Feiyao

AU - Quan, Hengdao

PY - 2016/4/20

Y1 - 2016/4/20

N2 - The mechanism of the halogen-transfer isomerization of halogenated cyclopentene was investigated over a NH4F catalyst in DMF. This catalytic system was to have the unique ability to isomerize halogenated cyclopentene selectively. The process of migration of the F atom in the 3-position on the C(sp3) atom to the 4-position on the C(sp3) atom is in chemical equilibrium, whereas the process of migration of the F atom in the 2-position on the C(sp2) atom to the 3-position on the C(sp3) atom is not. Therefore, halogenated cyclopentene containing fluorine on either the C(sp3) or C(sp2) atom could be prepared selectively in terms of the NH4F catalyst.

AB - The mechanism of the halogen-transfer isomerization of halogenated cyclopentene was investigated over a NH4F catalyst in DMF. This catalytic system was to have the unique ability to isomerize halogenated cyclopentene selectively. The process of migration of the F atom in the 3-position on the C(sp3) atom to the 4-position on the C(sp3) atom is in chemical equilibrium, whereas the process of migration of the F atom in the 2-position on the C(sp2) atom to the 3-position on the C(sp3) atom is not. Therefore, halogenated cyclopentene containing fluorine on either the C(sp3) or C(sp2) atom could be prepared selectively in terms of the NH4F catalyst.

KW - halogen transfer

KW - halogenated building block

KW - halogenated cyclopentene

KW - isomerization

KW - reaction mechanisms

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U2 - 10.1002/cctc.201600055

DO - 10.1002/cctc.201600055

M3 - Article

AN - SCOPUS:84978015851

SN - 1867-3880

VL - 8

SP - 1474

EP - 1478

JO - ChemCatChem

JF - ChemCatChem

IS - 8

ER -

Isomerization of Halogenated Cyclopentene over a NH₄F Catalyst

Abstract

Keywords

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