Reaction of nitroalcohols with sulfur tetrafluoride

Baum, Kurt

doi:10.1021/jo01267a099

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C(n02)3ch20cf31

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1969

2011

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Cited by 8 publications

(2 citation statements)

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“…A report in the Russian literature by Eremenko et al (3) on the preparation of 1-fluoro-1,1,3,3-tetranitro-5-oxahexane, III, prompts us to report our recent synthesis and characterization of this compound. 1 To whom correspondence should be addressed. When I was treated with 3% hydrogen peroxide and potassium hydroxide, Reaction 1, decomposition resulted.…”

Section: C(n02)3ch20cf3mentioning

confidence: 99%

Synthesis of 1-fluoro-1,1,3,3-tetranitro-5-oxahexane, 3-trifluoromethoxy-2,2-dinitropropanol, and 3-fluoro-2,2-dinitropropanol

Peters¹,

Simon²,

Ross³

et al. 1975

J. Chem. Eng. Data

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Section: C(n02)3ch20cf3mentioning

confidence: 99%

Synthesis of 1-fluoro-1,1,3,3-tetranitro-5-oxahexane, 3-trifluoromethoxy-2,2-dinitropropanol, and 3-fluoro-2,2-dinitropropanol

Peters¹,

Simon²,

Ross³

et al. 1975

J. Chem. Eng. Data

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“…(8) In the parent exo-norbornyl system the 7-isotope effect is the same for exo and endo deuterium at C-62•3 and there is evidence7 that these effects are additive, in which case the 7-isotope effect for the 6,6-dt-exo-…”

mentioning

confidence: 99%

.gamma.-Deuterium isotope effects in norbornyl systems

Goering¹,

Humski²

1969

J. Am. Chem. Soc.

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Fluorination by Sulfur Tetrafluoride

et al. 2011

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Although sulfur tetrafluoride is a remarkably versatile agent for selectively introducing fluorine atoms into organic compounds, its existence was doubted as late as 1950. A colorless gas boiling at ‐38o C, sulfur tetrafluoride was probably first made by treatment of sulfur with uranium hexafluoride and subsequently by the reaction of sulfur with cobalt(III) fluoride. Both products were of questionable purity. In 1950 sulfur tetrafluoride was unequivocally synthesized by electrical decomposition of trifluormethylsulfur pentafluoride. It was not until 1955 that gram amounts were prepared and thus making sulfur tetrafluoride a viable compound. This led the way for the discovery of its remarkable fluorinating ability. The ability of sulfur tetrafluoride to replace carbonyl oxygen selectively is probably the most useful synthetic application.

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Reaction of nitroalcohols with sulfur tetrafluoride

Cited by 8 publications

References 2 publications

Synthesis of 1-fluoro-1,1,3,3-tetranitro-5-oxahexane, 3-trifluoromethoxy-2,2-dinitropropanol, and 3-fluoro-2,2-dinitropropanol

Synthesis of 1-fluoro-1,1,3,3-tetranitro-5-oxahexane, 3-trifluoromethoxy-2,2-dinitropropanol, and 3-fluoro-2,2-dinitropropanol

.gamma.-Deuterium isotope effects in norbornyl systems

Fluorination by Sulfur Tetrafluoride

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