6713-49-1Relevant articles and documents
Stereodivergent synthesis of alkenes by controllable syn-/anti-fragmentation of β-hydroxysulfonyl intermediates
Górski, Bartosz,Basiak, Dariusz,Grzesiński, ?ukasz,Barbasiewicz, Micha?
supporting information, p. 7660 - 7663 (2019/08/30)
The reduction of the carbonyl group in acylated trifluoroethyl alkanesulfonates follows the Felkin-Ahn selectivity, and the so-formed diastereomeric β-hydroxysulfonyl intermediates undergo syn- and anti-fragmentation, depending on the reaction conditions. In effect, isomeric E- and Z-alkenes are formed in a stereodivergent manner, which mimics the mechanistic manifold of the Peterson olefination.
Carbonylation of organic halides with carbon monoxide mediated by samarium diiodide. Improvement and mechanistic investigations
Tomisaka, Yuri,Harato, Nami,Sato, Masahiro,Nomoto, Akihiro,Ogawa, Akiya
, p. 1444 - 1446 (2007/10/03)
Under an atmospheric pressure of carbon monoxide, photoinduced reductive carbonylation of organic halides (RX) with samarium diiodide (SmI2) occurs to afford the corresponding unsymmetrical ketones (RC(O)CH2R) in good yields. Mechanistic insight into this carbonylation, especially the pathway for the generation of an acylsamarium species (RC(O)SmI2) as a key intermediate, is also investigated in detail.
New coupling reactions of some acyl chlorides with samarium diiodide in the presence of samarium: Carbinols from three acyl units
Clausen, Christian,Weidner, Ingo,Butenschoen, Holger
, p. 3799 - 3806 (2007/10/03)
A mixture of samarium(II) iodide and samarium can induce a coupling reaction of three molecules of alkanoyl halide to give trialkylcarbinols of 2-hydroxy-1,3-diones. When aliphatic, unbranched alkanoyl chlorides are used, this new coupling reaction provides trimeric products as the main reaction products. Tetrahydropyran (THP) proved superior as the solvent because no ring-opening and subsequent reaction with the alkanoyl halides was observed under the reaction conditions, unlike when THF was used. Wiley-VCH Verlag GmbH, 2000.