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Preparation of Highly Fluorinated Cyclopropanes and Ring-Opening Reactions with Halogens
Abstract
Various highly fluorinated cyclopropanes 1 were prepared by reaction of the appropriate fluorinated olefins with hexafluoropropylene oxide (HFPO) at 180 degrees C. The fluorinated nitrile 1e was converted to the triazine derivatives 2a and 2b by catalysis with Ag(2)O and NH(3)/(CF(3)CO)(2)O, respectively. The fluorinated cyclopropanes reacted with halogens at elevated temperatures to provide the first useful, general synthesis of 1,3-dihalopolyfluoropropanes. At 150-240 degrees C, hexafluorocyclopropane and halogens X(2) produce XCF(2)CF(2)CF(2)X (X = Cl, Br, I) in 50-80% isolated yields. Pentafluorocyclopropanes c-C(3)F(5)Y [Y = Cl, OCF(3), OC(3)F(7) and OCF(2)CF(CF(3))OCF(2)CF(2)Z; Z = SO(2)F, CN, CO(2)Me] react regiospecifically at 150 degrees C to give XCF(2)CF(2)CFXY, c-C(3)F(5)Br reacts regioselectively with Br(2) to give a 16.7:1 mixture of BrCF(2)CF(2)CFBr(2):BrCF(2)CFBrCF(2)Br, whereas c-C(3)F(5)H reacts unselectively with I(2) to produce a statistical 2:1 mixture of ICF(2)CF(2)CFHI:ICF(2)CFHCF(2)I. Tri- and di(pentafluorocyclopropyl) derivatives 2 also undergo ring-opening reaction with halogens to give 16 and 17. Upon treatment of tetrafluorocyclopropanes 1j, 1k, and 1l with Br(2) or I(2), ring opening occurred exclusively at substituted carbons to give XCF(2)CF(2)CXY(2). Thermolysis of the ring-opened product ICF(2)CF(2)CFIOR(F) at 240 degrees C gave R(F)I and ICF(2)CF(2)COF in high yields.
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References 24 · Cited by 25
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Metadata
- Authors
- Yang, Z.-Y.
- Affiliations
- DuPont (United States) (US)
- Corresponding author
- Yang, Zhen-Yu
- ORCID
- Yang, Zhen-Yu
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-05-01
- Volume
- 68
- Issue
- 11
- Pages
- 4410-4416
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2000555021
- Cited by
- 25
- References
- 24
- Citations by year
- 2025: 3 · 2024: 1 · 2023: 2 · 2022: 2 · 2015: 3 · 2014: 1 · 2013: 2
- FWCI
- 1.43
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- The Journal of Organic Chemistry (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Fluorine in Organic Chemistry
- Physical Sciences › Chemistry › Organic Chemistry › Cyclopropane Reaction Mechanisms
- Physical Sciences › Environmental Science › Environmental Chemistry › Per- and polyfluoroalkyl substances research
- Keywords
- fluorinated cyclopropanes, ring-opening reactions, halogen addition, hexafluoropropylene oxide, fluorinated alkenes, triazines, regioselectivity, halogenation, thermal decomposition, fluorinated nitriles, organofluorine synthesis, trifluoromethyl compounds, trifluoromethyl ethers
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