Reaction of carbonyl compounds with xenon difluoride in the presence of silicon tetrafluoride

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

doi:10.1016/j.jfluchem.2003.11.019

Reaction of carbonyl compounds with xenon difluoride in the presence of silicon tetrafluoride

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

^*Corresponding author for this work

National Institute of Advanced Industrial Science and Technology

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

11 Citations (Scopus)

Abstract

Reaction of various carbonyl compounds with xenon difluoride in the presence of silicon tetrafluoride was investigated. Aromatic aldehyde, ketones, and α-ketoester react with xenon difluoride to give α,α-difluoroalkyl phenyl ethers. However, acid fluoride, ester, acid cyanide, α-ketocarboxylic acid, or thioester do not afford the corresponding products. In the case of cinnamaldehyde, fluorination was accompanied by intramolecular cyclization to afford fluorinated epoxide.

Original language	English
Pages (from-to)	705-709
Number of pages	5
Journal	Journal of Fluorine Chemistry
Volume	125
Issue number	5
DOIs	https://doi.org/10.1016/j.jfluchem.2003.11.019
Publication status	Published - May 2004
Externally published	Yes

Keywords

Carbonyl compound
Cinnamaldehyde
Cyclization
Fluorination
Rearrangement
Silicon tetrafluoride
Xenon difluoride

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10.1016/j.jfluchem.2003.11.019

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title = "Reaction of carbonyl compounds with xenon difluoride in the presence of silicon tetrafluoride",

abstract = "Reaction of various carbonyl compounds with xenon difluoride in the presence of silicon tetrafluoride was investigated. Aromatic aldehyde, ketones, and α-ketoester react with xenon difluoride to give α,α-difluoroalkyl phenyl ethers. However, acid fluoride, ester, acid cyanide, α-ketocarboxylic acid, or thioester do not afford the corresponding products. In the case of cinnamaldehyde, fluorination was accompanied by intramolecular cyclization to afford fluorinated epoxide.",

keywords = "Carbonyl compound, Cinnamaldehyde, Cyclization, Fluorination, Rearrangement, Silicon tetrafluoride, Xenon difluoride",

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

year = "2004",

month = may,

doi = "10.1016/j.jfluchem.2003.11.019",

language = "English",

volume = "125",

pages = "705--709",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier B.V.",

number = "5",

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TY - JOUR

T1 - Reaction of carbonyl compounds with xenon difluoride in the presence of silicon tetrafluoride

AU - Tamura, Masanori

AU - Matsukawa, Yasuhisa

AU - Quan, Heng Dao

AU - Mizukado, Junji

AU - Sekiya, Akira

PY - 2004/5

Y1 - 2004/5

N2 - Reaction of various carbonyl compounds with xenon difluoride in the presence of silicon tetrafluoride was investigated. Aromatic aldehyde, ketones, and α-ketoester react with xenon difluoride to give α,α-difluoroalkyl phenyl ethers. However, acid fluoride, ester, acid cyanide, α-ketocarboxylic acid, or thioester do not afford the corresponding products. In the case of cinnamaldehyde, fluorination was accompanied by intramolecular cyclization to afford fluorinated epoxide.

AB - Reaction of various carbonyl compounds with xenon difluoride in the presence of silicon tetrafluoride was investigated. Aromatic aldehyde, ketones, and α-ketoester react with xenon difluoride to give α,α-difluoroalkyl phenyl ethers. However, acid fluoride, ester, acid cyanide, α-ketocarboxylic acid, or thioester do not afford the corresponding products. In the case of cinnamaldehyde, fluorination was accompanied by intramolecular cyclization to afford fluorinated epoxide.

KW - Carbonyl compound

KW - Cinnamaldehyde

KW - Cyclization

KW - Fluorination

KW - Rearrangement

KW - Silicon tetrafluoride

KW - Xenon difluoride

UR - https://www.scopus.com/pages/publications/2342507636

U2 - 10.1016/j.jfluchem.2003.11.019

DO - 10.1016/j.jfluchem.2003.11.019

M3 - Article

AN - SCOPUS:2342507636

SN - 0022-1139

VL - 125

SP - 705

EP - 709

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

IS - 5

ER -

Reaction of carbonyl compounds with xenon difluoride in the presence of silicon tetrafluoride

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Keywords

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