Insertion reactions of difluorocarbene generated by pyrolysis of hexafluoropropene oxide to O-H bond

Junji Mizukado; Yasuhisa Matsukawa; Heng Dao Quan; Masanori Tamura; Akira Sekiya

doi:10.1016/j.jfluchem.2005.01.012

Insertion reactions of difluorocarbene generated by pyrolysis of hexafluoropropene oxide to O-H bond

Junji Mizukado^*, Yasuhisa Matsukawa, Heng Dao Quan, Masanori Tamura, Akira Sekiya

^*Corresponding author for this work

National Institute of Advanced Industrial Science and Technology

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

8 Citations (Scopus)

Abstract

ROCHF₂-type fluorinated ethers were synthesized by the reaction of hexafluoropropene oxide (HFPO) with alcohol or phenol. In this reaction, although the insertion reaction of difluorocarbene to OH bond and the nucleophilic attack of alcohol or phenol to HFPO were competition, the insertion reaction proceeded predominantly to give fluorinated ether in the case of low nucleophilic alcohol or phenol. In addition, high reaction pressure is advantageous to the selectivity of the fluorinated ethers in the reaction of HFPO with (CF₃)₂CHOH or C₆F₅OH.

Original language	English
Pages (from-to)	365-369
Number of pages	5
Journal	Journal of Fluorine Chemistry
Volume	126
Issue number	3
DOIs	https://doi.org/10.1016/j.jfluchem.2005.01.012
Publication status	Published - Mar 2005
Externally published	Yes

Keywords

Difluorocarbene
Fluorinated ether
Hexafluoropropene oxide
Insertion reaction

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10.1016/j.jfluchem.2005.01.012

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@article{5c73bd3aef904fe19ea4971f1fa3ccaf,

title = "Insertion reactions of difluorocarbene generated by pyrolysis of hexafluoropropene oxide to O-H bond",

abstract = "ROCHF2-type fluorinated ethers were synthesized by the reaction of hexafluoropropene oxide (HFPO) with alcohol or phenol. In this reaction, although the insertion reaction of difluorocarbene to OH bond and the nucleophilic attack of alcohol or phenol to HFPO were competition, the insertion reaction proceeded predominantly to give fluorinated ether in the case of low nucleophilic alcohol or phenol. In addition, high reaction pressure is advantageous to the selectivity of the fluorinated ethers in the reaction of HFPO with (CF3)2CHOH or C6F5OH.",

keywords = "Difluorocarbene, Fluorinated ether, Hexafluoropropene oxide, Insertion reaction",

author = "Junji Mizukado and Yasuhisa Matsukawa and Quan, {Heng Dao} and Masanori Tamura and Akira Sekiya",

year = "2005",

month = mar,

doi = "10.1016/j.jfluchem.2005.01.012",

language = "English",

volume = "126",

pages = "365--369",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier B.V.",

number = "3",

}

TY - JOUR

T1 - Insertion reactions of difluorocarbene generated by pyrolysis of hexafluoropropene oxide to O-H bond

AU - Mizukado, Junji

AU - Matsukawa, Yasuhisa

AU - Quan, Heng Dao

AU - Tamura, Masanori

AU - Sekiya, Akira

PY - 2005/3

Y1 - 2005/3

N2 - ROCHF2-type fluorinated ethers were synthesized by the reaction of hexafluoropropene oxide (HFPO) with alcohol or phenol. In this reaction, although the insertion reaction of difluorocarbene to OH bond and the nucleophilic attack of alcohol or phenol to HFPO were competition, the insertion reaction proceeded predominantly to give fluorinated ether in the case of low nucleophilic alcohol or phenol. In addition, high reaction pressure is advantageous to the selectivity of the fluorinated ethers in the reaction of HFPO with (CF3)2CHOH or C6F5OH.

AB - ROCHF2-type fluorinated ethers were synthesized by the reaction of hexafluoropropene oxide (HFPO) with alcohol or phenol. In this reaction, although the insertion reaction of difluorocarbene to OH bond and the nucleophilic attack of alcohol or phenol to HFPO were competition, the insertion reaction proceeded predominantly to give fluorinated ether in the case of low nucleophilic alcohol or phenol. In addition, high reaction pressure is advantageous to the selectivity of the fluorinated ethers in the reaction of HFPO with (CF3)2CHOH or C6F5OH.

KW - Difluorocarbene

KW - Fluorinated ether

KW - Hexafluoropropene oxide

KW - Insertion reaction

UR - http://www.scopus.com/inward/record.url?scp=15944393164&partnerID=8YFLogxK

U2 - 10.1016/j.jfluchem.2005.01.012

DO - 10.1016/j.jfluchem.2005.01.012

M3 - Article

AN - SCOPUS:15944393164

SN - 0022-1139

VL - 126

SP - 365

EP - 369

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

IS - 3

ER -

Insertion reactions of difluorocarbene generated by pyrolysis of hexafluoropropene oxide to O-H bond

Abstract

Keywords

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