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Updated: Aug 21, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
The structure of aqueous pentaoxo silicon complexes with cis-1,2-dihydroxycyclopentane and furanoidic vicinal
Stephen D Kinrade1, Raymond J Balec, Andrew S Schach
1Dept. of Chemistry, Lakehead University, 955 Oliver Road, Thunder Bay, Ontario P7B 5E1, Canada. Stephen.Kinrade@lakeheadu.ca
Abstract:
Addition of cis-1,2-dihydroxycyclopentane to aqueous alkaline silicate solutions results in the spontaneous formation of three organosilicate species, each with a 2:1 ligand to Si ratio and a pentacoordinated silicon centre. By using a mixture of both cis-1,2-dihydroxycyclopentane and 1,4-anhydroerythritol we show unambiguously that all three species are diastereomers of the monomeric bis(diolato)-hydroxo complex, [(L=)(2)SiOH](-)(where L represents the cis-diol ligand), thus clarifying the general assignment of (29)Si NMR spectra reported for silicate solutions containing furanoidic sugars with vicinal cis-diol functionality, such as ribose.
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