Oxymetallation. Part II. The t-butyl peroxymercuration and methoxymercuration of αβ-unsaturated ketones and esters
Abstract
The products of both t-butyl peroxymercuration and methoxymercuration of six αβ-unsaturated ketones and seven αβ-unsaturated esters have been characterised. The structures of the oxymercurials are deduced from their 1H n.m.r. spectra on the basis of chemical shifts and 199Hg coupling constants. Where the ketones and esters are alkylated solely at the carbon α to the carbonyl group, the mercury becomes attached to the carbon β to the carbonyl group (β-mercuration); for all other compounds, α-mercuration is obtained. The reactions are compared with other electrophilic additions to αβ-unsaturated carbonyl compounds.