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36.12.9.1.3 Method 3: Rearrangement of a Carbolithiate

DOI: 10.1055/sos-SD-036-00789

Morey, J. V.; Wheatley, A. E. H.Science of Synthesis, (2008361129.

Many substrates that contain CH groups in close proximity to oxygen combine straightforwardly with an organolithium reagent to give an α-oxy carbometalate. These carbanionic systems are well known to rearrange via OX bond cleavage accompanied by migration of the metal to produce an alcoholate. The clear synthetic utility of these rearrangements lies in their ability to correspondingly generate a new CX bond (Scheme 32).

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