A-Lithiated styrene oxide

The dichotomous (carbanionic/carbene-like) reactivity exhibited by a-Uthiated styrene oxides has been thoroughly investigated in solution by means of a multinuclear magnetic resonance study supported by DFT calculations. In particular, in the case of a-lithiated styrene oxide 20, it was ascertained that an O-coordinated bridged dimer such as 20B does have a stronger carbenoid character than the monomer 20A. This is consistent with both the higher Ca—O bond elongation predicted by calculations. 

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