Abstract
One of the most highly strained bridghead alkenes—bridgehead olefin A, a trans cyclopentene analogue—has been trapped by MeLi and, in an ene reaction, by α-methylstyrene. DFT calculations have shown that A is a local minimum on the corresponding energy hypersurface, but that rearrangement of A to carbene B (X = Cl) needs an energy barrier of only 8.4 kcal mol−1.
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