Aqueous Permanganate Oxidations of Cycloalkenes to cis-Glycols and Cis to Trans Conversions

A series of cis-glycols including 1,2-cyclopentanediol, 1-methyl-1,2-cyclopentanediol, 1,2-dimethyl-1,2-cyclopentanediol, 1,2-cyclohexanediol, 1-methyl-1,2-cyclohexanediol, 1,2-dimethyl-1,2-cyclohexanediol, 1,2-cycloheptanediol, 1,2-cyclooctanediol, exo,exo-bicyclo[2.2.1]heptane-2,3-diol, and bicycl...

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Bibliographic Details
Published in:Organic process research & development 1998-05, Vol.2 (3), p.147-150
Main Authors: Taylor, Jay E, Janini, Thomas E, Elmer, Otto C
Format: Article
Language:English
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Summary:A series of cis-glycols including 1,2-cyclopentanediol, 1-methyl-1,2-cyclopentanediol, 1,2-dimethyl-1,2-cyclopentanediol, 1,2-cyclohexanediol, 1-methyl-1,2-cyclohexanediol, 1,2-dimethyl-1,2-cyclohexanediol, 1,2-cycloheptanediol, 1,2-cyclooctanediol, exo,exo-bicyclo[2.2.1]heptane-2,3-diol, and bicyclo[2.2.2]octane-2,3-diol have been prepared by permanganate oxidations of cycloalkenes using a turbulent stirring technique. Conditions for the reactions, methods of purification, and yields are presented. Both hydroxide ion and an aqueous environment are highly essential to the formation of glycols. Excessive solvent decreases yields. A procedure for converting certain cis- to trans-glycols is given. A preparation for very pure Δ9,10-octalin is included.
ISSN:1083-6160
1520-586X
DOI:10.1021/op9701189