17101-71-2Relevant articles and documents
Halodecarboxylation of α,β-acetylenic and α,β-ethylenic acids
Homsi, Fadi,Rousseau, Gerard
, p. 1495 - 1498 (2007/10/03)
Reaction of bis(collidine)iodine(I) (or bromine (I)) hexafluorophosphate with acetylenic acids led to the corresponding iodo(or bromo)acetylenes in high yields. This halodecarboxylation reaction was also observed with acrylic acids substituted in position 3 by an aryl group or an heteroatom.
Asymmetric cross-coupling reactions: enantioselective synthesis of alkenyl sulphides
Cardellicchio, Cosimo,Fiandanese, Vito,Naso, Francesco
, p. 11 - 16 (2007/10/02)
An enantioselective synthesis of alkenyl sulphides by cross-coupling reactions between (E)-or (Z)-1-arylthio-2-bromoethenes and Grignard or organozinc reagents, using chiral complexes as catalysts, is described.The process has been found to be sensitive to several factors, such as the nature of the substrate, the organometallic reagent, the ligand, and the metal complex used as catalyst.Optical purities up to 57percent were obtained.The resulting unsaturated thioesters have been transformed into optically active 1-alkyl-2-phenyl-ethenes or 2-phenylpropionic acid.A new method for the synthesis of the starting (Z)-1-arylthio-2-bromoethenes is also reported
NUCLEOPHILIC REACTION AT A VINYL CENTER. XXII. SYNTHESIS AND NUCLEOPHILIC VINYLIC SUBSTITUTION IN E-β-FLUOROVINYL ARYL SULFONES
Shainyan, B. A.,Mirskova, A. N.
, p. 61 - 66 (2007/10/02)
The reaction of potassium fluoride with E-β-bromovinyl aryl sulfones in the presence of 18-crown-6-ether leads to a mixture of the sulfones XC6H4SO2CH2CHF2 and E-XC6H4SO2CH=CHF, the ratio of which decreases in the order X=CH3, H, Cl, NO2.The kinetics of n
NUCLEOPHILIC REACTIONS AT A VINYLIC CENTER. XX. BASE-CATALYZED REARRANGEMENT OF ARYL β,β-DIBROMOVINYL SULFONES TO Z-ARYL α,β-DIBROMOVINYL SULFONES
Shainyan, B. A.,Mirskova, A. N.
, p. 224 - 229 (2007/10/02)
A series of aryl β,β-dibromovinyl sulfones XC6H4SO2CH=CBr2 were synthesized, and their rearrangement to Z-aryl α,β-dibromovinyl sulfones XC6H4SO2CBr=CHBr by the action of KF.18-crown-6 in benzene was studied.The rearrangement rate increases with increase in the concentration of the base -> and with increase in the electron-withdrawing character of the substituent X and does not depend on the temperature.
NUCLEOPHILIC REACTIONS AT VINYL CENTER. VIII. SYNTHESIS AND PROPERTIES OF β,β-DIBROMOVINYL PHENYL SULFONE
Shainyan, B. A.,Mirskova, A. N.
, p. 443 - 446 (2007/10/02)
The radical reaction of tribromoethylene with thiophenol was investigated.In addition to the main product, β,β-dibromovinyl phenyl sulfide, 15-30percent (depending on the conditions) of a mixture of isomeric β-bromovinyl phenyl sulfides is formed. β,β-Dibromovinyl phenyl sulfone was obtained by the oxidation of dibromovinyl phenyl sulfide, and it readily enters into nucleophilic vinyl substitution of both bromine atoms.During comparison of its reactivity with the reactivity of the previously investigated dichlorovinyl phenyl sulfone a clearly defined "element-effect" was detected, indicating cleavage of the C-Hlg bond at the rate-determining stage.
