alpha -Nitro ketones. 6. Synthesis and conformation of 2-methyl-2-nitro-, cis- and trans-6-methyl-2-nitro-, and cis- and trans-2,6-dimethyl-2-nitrocyclohexanones.

Nitration of the most substituted (thermodynamically more stable ) enol acetate or trimethylsilyl ether of 2-methylcyclohexanone (I) and the phase-transfer methylation of 2-nitrocyclohexanone serve as methods of prepn. of 2-methyl-2-nitrocyclohexanone (II); nitration of the least substituted enol ac...

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Journal Title: Journal of Organic Chemistry Vol. 47; no. 7; pp. 1176 - 1181
Authors: Pimchit Dampawan, Walter W. Zajac
Format: Article
Published: 1982
Application Date: Dep. Chem.,Villanova Univ.,Villanova,PA,USA.
Subjects:
Summary: Nitration of the most substituted (thermodynamically more stable ) enol acetate or trimethylsilyl ether of 2-methylcyclohexanone (I) and the phase-transfer methylation of 2-nitrocyclohexanone serve as methods of prepn. of 2-methyl-2-nitrocyclohexanone (II); nitration of the least substituted enol acetate or trimethylsilyl ether of I and methylation of the dianion of II lead to cis- and trans-6-methyl-2-nitrocyclohexanone. Nitration of the enol acetate or trimethylsilyl ether of 2,6-dimethylcyclohexanone and methylation of either 2-methyl-2-nitro- or 6-methyl-2-nitrocyclohexanone are methods of prepn. of cis- and trans-2,6-dimethyl-2-nitrocyclohexanone. 1H NMR chem. shift and coupling const. data were used to det. the preferred conformations of the cyclohexanones: 2(e)-methyl-2(a)-nitro; cis-6(e)-methyl-2(e)-nitro; trans-6(e)-methyl-2(a)-nitro; cis-2(e),6(e)-dimethyl-2(a)-nitro; trans-2(a)-methyl-6(e)-methyl-2(e)-nitro.
ISSN: 0022-3263