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The Oxidative Cyclization of 2,5-Dihydroxyphenylalkylamines to 5-Hydroxyindoles and 6-Hydroxyquinolines 1

โœ Scribed by Moore, James A.; Capaldi, Eugene C.


Book ID
120216693
Publisher
American Chemical Society
Year
1964
Tongue
English
Weight
687 KB
Volume
29
Category
Article
ISSN
0022-3263

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Oxidative cyclization of 1,4-dienes to y
โœ Benjamin Travis; Babak Borhan ๐Ÿ“‚ Article ๐Ÿ“… 2001 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 112 KB

KMnO 4 and OsO 4 catalyze the oxidative cyclization of 1,4-dienes to provide 2,3,5-trisubstituted tetrahydrofuran-diols in 30% yield. This reaction proceeds stereoselectively via a proposed [3+2] cycloaddition. Competing oxidative pathways are the major non-productive processes that reduce the yield