2344-09-4Relevant academic research and scientific papers
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.
, p. 3167 - 3179 (2018)
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.
A remarkable [2.2.2] propellane
He, Yigang,Junk, Christopher P.,Cawley, John J.,Lemal, David M.
, p. 5590 - 5591 (2007/10/03)
To explore the effects of fluorine substitution on the highly strained [2.2.2]propellane skeleton, a new representative of this ring system, perfluorotricyclo[2.2.2.01,4]octan-2-one ethylene ketal, was prepared by a rapid and quantitative [2+2] cycloaddition to the strained alkene perfluorobicyclo[2.2.0]hex-1(4)-ene. The propellane displays impressive thermal stability, and the vulnerable C-C bond joining the bridgeheads is very resistant to attack by electrophilic reagents. On the other hand, that electron-deficient bond is cleaved quickly at room temperature by a variety of nucleophiles and mild reducing agents. The behavior of this compound contrasts dramatically with that of the only known [2.2.2]propellane lacking fluorine substituents. Copyright
Halogenated 1,3-dioxolanes and derivatives
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, (2008/06/13)
There are disclosed halogenated dioxolanes of a specified formula, dioxoles made therefrom, polymers of the dioxoles, and processes for making the dioxolanes.
