Cyclopropyl carbinols oxidative rearrangement

Due to the higher oxidation level cyclopropylcarbinyl-homoallyl rearrangement (see also Section IV.C) of oxycyclopropanes gives, y-unsaturated carbonyl compounds. This feature has been discovered by Julia and coworkers, who reacted certain esters with Grignard reagents or LiAlH4. The corresponding cyclopropyl carbinol opens under acidic conditions to j5,y-unsaturated aldehydes (equation This conversion also works for... [Pg.396]

JAROUSSE MAKOSZA Phase transler 189 JEGERTetrahydroluran synthesis 190 JOHNSON Phenol alkynylation 191 Johnson 168,197,240 JONES Oxidation reagent 192 JULIA BRUYLANTS Cyclopropyl carbinol rearrangement 193... [Pg.225]

Ph3Si ethylene oxide catalytically adds PhSH to give a- and -adducts in 6 1 ratio, and serves as a vinyl dication equivalent with RCu to give alkenes stereoselectively, while epoxides rearrange in the presence of silylated nucleophiles Diphenylmethylsilylation of cyclopropane carboxylates gives the C-silylated ester which then form C-silylated cyclopropyl ketones, P-silyl cyclopropyl carbinols, and alkylidene cyclopropancs, which ring expand to the... [Pg.90]