Add time:08/06/2019         Source:sciencedirect.com

Upon treatment with the superbasic 1 : 1 mixture of butyllithium and potassium tert-butoxide cis- and trans-1,1,1-triphenyl-2-butene as well as 4,4,4-triphenyl-1-butene undergo a hydrogen/metal exchange to afford 1-(triphenylmethyl)allyl potassium [4,4,4-triphenyl-2-butenyl potassium] which can exist in two stereoisomeric forms. Torsional equilibration leads to an endo/exo-ratio of approximately 50 : 50. Novel endo-stabilizing interactions are discussed to rationalize this result. At temperatures around or above 0°C a phenyl 1,2-migration, though no 1,4-migration takes place.

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