Related Experiment Video
Updated: Aug 25, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Reaction of tin porphyrins with vicinal diols
Guodong Du1, Arkady Ellern, L Keith Woo
1Department of Chemistry, Iowa State University, Ames, Iowa 50011-3111, USA.
Abstract:
Reactions of tin porphyrins with vicinal diols were investigated. Treatment of (TTP)Sn(CCPh)(2) or (TTP)Sn(NHtolyl)(2) with pinacol and 2,3-diphenylbutane-2,3-diol afforded diolato complexes (TTP)Sn[OC(Me)(2)C(Me)(2)O] (1) and (TTP)Sn[OC(Ph)(Me)C(Ph)(Me)O] (2), respectively. Both complexes underwent C-C cleavage reactions to give (TTP)Sn(II) and ketones. Reaction of (TTP)Sn(CCPh)(2) with 1 equivalent of o-catechol generated (TTP)Sn(CCPh)(OC(6)H(4)OH) (3), which subsequently transformed into (TTP)Sn(OC(6)H(4)O) (4). With excess catechol, disubstituted (TTP)Sn(OC(6)H(4)OH)(2) (5) was obtained. (TTP)Sn(CCPh)(OCHRCHROH) (R = H, 6; R = Ph, 8) and (TTP)Sn(OCHRCHROH)(2) (R = H, 7; R = Ph, 9) were obtained analogously by treatment of (TTP)Sn(CCPh)(2) with appropriate diols. In the presence of dioxygen, tin porphyrin complexes were found to promote the oxidative cleavage of vicinal diols and the oxidation of alpha-ketols to alpha-diketones. Possible reaction mechanisms involving diolato or enediolato intermediates are discussed. The molecular structure of (TTP)Sn(CCPh)(OC(6)H(4)OH) (3) was determined by X-ray crystallography.
More Related Videos
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
12:43The Synthesis of [Sn10(Si(SiMe3)3)4]2- Using a Metastable Sn(I) Halide Solution Synthesized via a Co-condensation Technique
Published on: November 28, 2016
Related Concept Videos
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids