Selective rhenium-catalyzed oxidation of secondary alcohols with methyl sulfoxide in the presence of ethylene glycol, a convenient one-pot synthesis of ketals

Organic Letters

Volumn 1, Issue 5, 1999, Pages 769-771

  Arterburn, Jeffrey B ^a   Perry, Marc C ^a  

^a NEW MEXICO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000007850     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990755e     Document Type: Article

References (32)

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21. 4, and purified by chromatography or bulb-to-bulb distillation. Method B. 2,4,6-Collidine (3.3 μL, 0.025 mmol) was also included. Ketones were efficiently converted to the ketals when they were added to the reaction mixture.
22. Ethylene glycol was consumed slowly during the reaction.
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30. Reaction mixtures containing 1,3-propanediol, a ligand with a larger "bite angle", were not effective for oxidizing alcohols. Interestingly, diol 1 also reacted with the catalyst and DMSO in the absence of ethylene glycol to produce ketone 2. This observation is consistent with the enhanced chelating ability of this diol relative to 1,3-propanediol due to the Thorpe-Ingold effect.
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