Journal of Organic Chemistry 2009-Mar
The effect of fluorine substitution on ring inversion in bicyclo[1.1.0]butanes.
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Abstract
Degenerate ring inversion in bicyclo[1.1.0]butane and eight of its fluorinated derivatives has been studied at the B3LYP/6-311G**+ level of theory. Fluorine substitution lowers the inversion barrier impressively; reasons for this phenomenon are discussed.