318967-94-1Relevant articles and documents
Stereoselective Halo-Succinimide Facilitated α-Halogenations of Substituted α-Trialkylsilyl-β-Substituted-α,β-Unsaturated Esters
Jennings, Michael P.,Probasco, Kristina C.
, p. 8945 - 8954 (2021/07/20)
The NXS (X = Cl, Br)-mediated halogenation of a series of (E)-α-trimethylsilyl-β-alkyl(aryl)-α,β-unsaturated esters in dimethylformamide (DMF) has furnished (Z)-β-substituted-α-halogenated-α,β-unsaturated ester products in moderate to high isolated yields (58-90%) with dr values of >20:1 coupled with the inversion of olefin stereochemistry. The reaction process was hypothesized to include an initial halonium cation intermediate, followed by regioselective ring opening with DMF. Subsequentanti-E2-type concomitant elimination allowed for the stereoselective formation of the product vinylic bromo-and chloroesters.
Stereoselective preparation of (E)-α-bromoacrylates from mixtures of brominated ando phosphonates
Olpp, Thomas,Brueckner, Reinhard
, p. 2135 - 2152 (2007/10/03)
We prepared 69:31-11:89 mixtures of phosphonates 6b and 7b containing two phenoxy substituents, a CO2Et group, and 1 or 2 bromine atoms, respectively, at the interspersed methylene group. Deprotonating 64:36 mixtures of these reagents with NaH
