413615-58-4Relevant articles and documents
Access to functionalized cyclopropylcarbinyl compounds from homoallylic ethers via zirconocene intermediates
Vasse, Jean-Luc,Szymoniak, Jan
, p. 6449 - 6451 (2007/10/03)
Cyclopropylcarbinylzirconium complexes were generated from homoallylic ethers and zirconocene (Cp2ZrCl2/2n-BuLi). They underwent further in situ transformations that is, bromination-substitution, transmetallation-functionalization and insertion reactions to afford various cyclopropylcarbinyl derivatives. In contrast, ring-opening products could be selectively obtained by treating the zirconium complex with MeLi, prior to functionalization.
Iodine(V) reagents in organic synthesis. Part 4. o-Iodoxybenzoic acid as a chemospecific tool for single electron transfer-based oxidation processes
Nicolaou,Montagnon,Baran,Zhong
, p. 2245 - 2258 (2007/10/03)
o-Iodoxybenzoic acid (IBX), a readily available hypervalent iodine(V) reagent, was found to be highly effective in carrying out oxidations adjacent to carbonyl functionalities (to form α, β-unsaturated carbonyl compounds) and at benzylic and related carbon centers (to form conjugated aromatic carbonyl systems). Mechanistic investigations led to the conclusion that these new reactions are initiated by single electron transfer (SET) from the substrate to IBX to form a radical cation which reacts further to give the final products. Fine-tuning of the reaction conditions allowed remarkably selective transformations within multifunctional substrates, elevating the status of this reagent to that of a highly useful and chemoselective oxidant.