75142-67-5Relevant articles and documents
β-Silylcarbonyl Compounds as Masked Enones
Fleming, Ian,Goldhill, Jon
, p. 1493 - 1498 (2007/10/02)
β-Trimethylsilylketones and lactones can be brominated (3)->(4) and desilylbrominated (4)->(5) specifically to place a double bond between the carbonyl group and the β-carbon atom to which the silicon had originally been bound.The silyl group therefore is a base- and acid stable group masking the α,β-unsaturation of enones.Several α-methylene-ketones and -lactones have been prepared in this way.With ketones, the bromination step seems always to introduce bromine mainly or exclusively at the α-position on that side of the ketone on which the β-silyl group is placed, regardless of whether it is more or the less substituted α-position.