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Open Access research which pushes advances in bionanotechnology

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SIPBS is a major research centre in Scotland focusing on 'new medicines', 'better medicines' and 'better use of medicines'. This includes the exploration of nanoparticles and nanomedicines within the wider research agenda of bionanotechnology, in which the tools of nanotechnology are applied to solve biological problems. At SIPBS multidisciplinary approaches are also pursued to improve bioscience understanding of novel therapeutic targets with the aim of developing therapeutic interventions and the investigation, development and manufacture of drug substances and products.

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Metal-free reductive cleavage of c-o sigma-bonds in acyloin derivatives by an organic neutral super-electron-donor

Cutulic, S.P.Y. and Findlay, N.J. and Zhou, S.Z. and Chrystal, E.J.T. and Murphy, J.A. (2009) Metal-free reductive cleavage of c-o sigma-bonds in acyloin derivatives by an organic neutral super-electron-donor. Journal of Organic Chemistry, 74 (22). pp. 8713-8718. ISSN 0022-3263

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Abstract

Neutral organic electron-donor 7, formally a pyridinylidene carbene dimer, effects reductive cleavage of C-O sigma-bonds in acyloin derivatives Ar(CO)CRR'OX (X = OAc, OPiv, OBz, OMs) and this represents the first cleavage of C-O sigma-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.