87456-65-3Relevant articles and documents
Metal-free reductive cleavage of C-O σ-bonds in acyloin derivatives by an organic neutral super-electron-donor
Cutulic, Sylvain P. Y.,Findlay, Neil J.,Zhou, Sheng-Ze,Chrystal, Ewan J. T.,Murphy, John A.
supporting information; experimental part, p. 8713 - 8718 (2009/12/28)
(Chemical Equation Presented) Neutral organic electron-donor 7, formally a pyridinylidene carbene dimer, effects reductive cleavage of C-O σ-bonds in acyloin derivatives Ar(CO)CRR′OX (X = OAc, OPiv, OBz, OMs) and this represents the first cleavage of C-O σ-bonds by a neutral organic electron-donor. The methodology is applicable to a large array of substrates and the reduced counterparts were isolated in good to excellent yields. For certain substrates, donor 7 behaves as a base, effecting condensation reactions with some acetate ester derivatives of acyloins, leading to butenolides. The variation in reactivity among the different substrates was rationalized. 2009 American Chemical Society.
