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Reactions in dry media. A simple conversion of nitro groups into carbonyls

โœ Scribed by Keinan, Ehud; Mazur, Yehuda


Book ID
126423978
Publisher
American Chemical Society
Year
1977
Tongue
English
Weight
809 KB
Volume
99
Category
Article
ISSN
0002-7863

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Possible neighbouring group participatio
โœ Michael J. Donaghy; Stephen P. Stanforth ๐Ÿ“‚ Article ๐Ÿ“… 2005 ๐Ÿ› Journal of Heterocyclic Chemistry ๐ŸŒ English โš– 79 KB

The alcohol 12 reacted with 4-toluenesulfonyl chloride in boiling dichloromethane solution to give the chlorinated product 13 rather than the expected tosylate 3 by a mechanism that could involve neighbouring group participation of the nitro-substituent. In contrast, the isomeric alcohol 15 reacted