The oxidative ring cleavage of 2-nitrocycloalkanones provides an efficient entry to a new class of functionalized compounds, namely methyl ö,ö-dichloronitro- ö-alkanoates. These compounds can be denitrated to afford the corresponding methyl ö,ö-dichloroalkanoates or allylated, giving a selective substitution of the nitrogroup by the allyl framework. The corresponding ö,ö-dibromo-ö-nitro esters behave differently with tin reagents, suffering the removal of the halogen atoms.
Oxidative Ring Cleavage of 2-Nitrocycloalkanones: Synthesis and Radical Induced Transformations of Methyl ω,ω-Dihalo-ω-nitroalkanoates
BALLINI, Roberto;PETRINI, Marino;
1996-01-01
Abstract
The oxidative ring cleavage of 2-nitrocycloalkanones provides an efficient entry to a new class of functionalized compounds, namely methyl ö,ö-dichloronitro- ö-alkanoates. These compounds can be denitrated to afford the corresponding methyl ö,ö-dichloroalkanoates or allylated, giving a selective substitution of the nitrogroup by the allyl framework. The corresponding ö,ö-dibromo-ö-nitro esters behave differently with tin reagents, suffering the removal of the halogen atoms.File in questo prodotto:
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