alpha -Nitro ketones. 5. Synthesis of 2-nitrocyclopentanones.

trans-3-Methyl, trans-trans- and trans-cis-3,4-dimethyl-, trans-3,5,5-trimethyl-, and cis- and trans-5-methyl-2-nitrocyclopentanones were prepd. by nitration of substituted cyclopentanone enol acetates with HNO3 at 15 Deg and by nitration of potassium enolates of the substituted cyclopentanones with...

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Journal Title: Journal of Organic Chemistry Vol. 46; no. 25; pp. 5151 - 5155
Authors: Walter W. Zajac, Fadia E. Elfehail
Format: Article
Published: 1981
Application Date: Dep. Chem.,Villanova Univ.,Villanova,PA,USA.
Subjects:
Summary: trans-3-Methyl, trans-trans- and trans-cis-3,4-dimethyl-, trans-3,5,5-trimethyl-, and cis- and trans-5-methyl-2-nitrocyclopentanones were prepd. by nitration of substituted cyclopentanone enol acetates with HNO3 at 15 Deg and by nitration of potassium enolates of the substituted cyclopentanones with amyl nitrate in THF. The stereochem. of the nitration reactions was discussed. The 2-nitrocyclopentanones undergo reactions with acid that make their isolation difficult.
ISSN: 0022-3263