Chemistry of the Highly Strained Alkene Perfluorobicyclo[2.2.0]hex‐1(4)‐ene

Junk, Christopher P.; He, Yigang; Zhang, Yin; Smith, Joshua R.; Dixon, David A.; Vasiliu, Monica; Lemal, David M.

doi:10.1002/ejoc.201800058

Title: Chemistry of the Highly Strained Alkene Perfluorobicyclo[2.2.0]hex‐1(4)‐ene

Journal Article · Thu Jun 21 00:00:00 EDT 2018 · European Journal of Organic Chemistry

DOI:https://doi.org/10.1002/ejoc.201800058· OSTI ID:1456247

Junk, Christopher P. ^[1]; He, Yigang ^[1]; Zhang, Yin ^[1]; Smith, Joshua R. ^[1]; Dixon, David A. ^[2]; Vasiliu, Monica ^[2];

^[1]

Department of Chemistry Dartmouth College 03755 Hanover NH USA
Department of Chemistry and Biochemistry University of Alabama 35487 Tuscaloosa AL USA

Several varieties of cycloaddition as well as nucleophilic and free radical addition to the highly reactive central bond of the title fluorocarbon ( 1 ) are described. [2 + 2] Cycloaddition to 1 has made available four of the five known representatives of the [2.2.2]propellane ring system, which are rare because of their extreme strain (in the absence of fluorine substitution) and high reactivity. Two of these, a propellanone and a propellene, are first reported here. Quantum mechanical calculations have shed light on many of these transformations.

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Sponsoring Organization:: USDOE

OSTI ID:: 1456247

Journal Information:: European Journal of Organic Chemistry, Journal Name: European Journal of Organic Chemistry Vol. 2018 Journal Issue: 24; ISSN 1434-193X

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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Cited by: 2 works

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