10563-09-4Relevant academic research and scientific papers
A new method for the activation of ethyl benzenesulfenate in electrophilic addition reactions
Zyk,Gavrilova, A. Yu.,Mukhina,Bondarenko,Zefirov
experimental part, p. 2572 - 2578 (2010/05/02)
Reactions of unsaturated compounds with the PhSOEt-SOHal2 and PhSOEt-Me3SiHal systems (Hal = Cl or Br) were proposed as a new route to haloalkyl phenyl sulfides. With acyclic and mono- and bicyclic alkenes and dienes as examples, the
Elimination and Addition Reactions. Part 37. A Comparative Study of Electronic, Steric , and Solvent Effects upon Reactivity in Additions of Benzenesulphenyl Chloride to Alkenes
Jones, G. Alun,Stirling, Charles J. M.,Bromby, Norman G.
, p. 385 - 394 (2007/10/02)
Rates of additions of benzenesulphenyl chloride to 35 alkenes in several solvents have been measured, and the products of the reactions have in most cases been identified.Results for arylalkenes broadly confirm previous work, but the responses to solvent change are not uniform throughout.The reactivity of bridged cycloalkanes is substantially greater than that of cycloalkenes, but that of cyclo-pentadiene dimer is anomalously small.For allylic substrates, the correlation of electron density at the double bond with reactivity is shown by a rectilinear relationship between log k and ?I.Allyl iodide and allyl alcohol are anomalously more reactive than this correlation would predict; this is accounted for by solvation and by internal solvation effects respectively.
Addition of arenesulphenyl chlorides to 2-methylenebicyclohept-5-ene: effect of increasing electron demand upon the rate and product determining transition states
Garratt, Dennis G.,Beaulieu, Pierre L.,Morisset, Veronique M.
, p. 1021 - 1029 (2007/10/02)
The rates and products of addition of a series of sixteen arenesulphenyl chlorides to 2-methylenebicyclohept-5-ene, 7, and the E,Z isomeric 2-ethylidenebicyclohept-5-enes, 8, and 9, have been determined in methylene chloride solution.The major species from attack on 7 is always endo-3-arylthio-1-chloromethyltricyclo2,6>heptane, the product of exo attack upon the endocyclic double bond with homoallylic participation of the exocyclic Π system.No evidence was found for initial electrophilic attack upon the exocyclic double bond.
