Organometallics

Aluminum's breakup with fluoroalkenes

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Science  25 May 2018:
Vol. 360, Issue 6391, pp. 871
DOI: 10.1126/science.360.6391.871-b

Carbon-fluorine bonds are hard to break. As a result, remediation of fluorocarbon waste streams is an enduring challenge. Bakewell et al. explored C–F scission in a variety of fluorinated propene derivatives by using an unusual synthetic aluminum compound. The electron-rich compound, with Al in the +1 oxidation state, inserted into both olefinic and allylic C–F bonds to form Al(III) products that were characterized crystallographically. Theory implicated two simultaneous competing mechanisms, respectively involving stereoretentive direct oxidative addition and stereoinverting intermediacy of a metallocyclopropane.

Angew. Chem. Int. Ed. 10.1002/anie.201802321 (2018).

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