58202-75-8Relevant academic research and scientific papers
Efficient preparation of E-β-iodovinyl phenylsulfone by finkelstein reaction at a vinylic center
Zoller,Uguen,De Cian,Fischer
, p. 8089 - 8092 (2007/10/03)
Treatment of E-β-chlorovinyl phenylsulfone, a crystalline compound that can be conveniently prepared on a large scale from 1,1,2-trichloroethane, by sodium iodide in acetone at ca 130 °C, in a sealed vessel, affords the title iodosulfone in good yield.
Reactions of Alkylmercurials with Heteroatom-Centered Acceptor Radicals
Russell, Glen A.,Ngoviwatchai, Preecha,Tashtoush, Hasan I.,Pla-Dalmau, Anna,Khanna, Rajive K.
, p. 3530 - 3538 (2007/10/02)
The relative reactivities of alkylmercury halides toward PhS., PhSe., or I. decrease drastically from R = tert-butyl to R = sec-alkyl to R = n-butyl, indicative that R. is formed in the rate-determining step in the attack of these radicals upon RHgCl.The alkyl radicals thus formed will enter into chain reactions in which a heteroatom-centered radical (A.) is regenerated from substrates such as RS-SR, ArSe-SeAr, ArTe-TeAr, PhSe-SO2Ar, Cl-SO2Ph; ZCH=CHA (A = Cl, I, SPh, SO2Ph); or PhCCHA (A = I, SPh, SO2Ph). β-Styrenyl (PhCH=CHA, Ph2C=CHA) and β-phenethynyl (PhCCA) systems with A = I, Br, SO2Ph also enter into chain reactions with mercury(II) salts with the ligands PhS, PhSe, PhSO2, or (EtO)2PO.The relative reactivities of a series of reagents toward t-Bu. and of PhCH=CHA, Ph2C=CHA, and PhCCA toward c-C6H11. are reported as well as the regioselectivity of t-Bu. attack observed for 1,2-disubstituted ethylenes (ZCH=CHA) with Z and A from the group Ph, Cl, Br, I, SO2Ph, SPh, Bu3Sn.Reactions of (E)- and (Z)-PhCH=CHI or MeO2CCH=CHI with t-Bu. or c-C6H11. occurred in a regioselective and stereospecific (retention) manner.Reactions of (E)- and (Z)-ClCH=CHCl occurred in a nonstereospecific manner in which the E/Z product ratio increased with the bulk of the attacking radical.A similar effect on the E/Z product ratios was observed for (Z)-MeO2CCH=CHCl.
NUCLEOPHILIC REACTIONS AT A VINYLIC CENTER. XV. A NEW 1,2-SIGMATROPIC REARRAGMENT IN VINYL ANIONS
Shainyan, B. A.,Mirskova, A. N.,Vitkovskii, V. Yu.
, p. 877 - 884 (2007/10/02)
The reactions of a series of β,β-dihalogenovinyl sulfones with potassium fluoride in benzene in the presence of 18-crown-6 ether were investigated.It was found that they undergo isomerization under the indicated conditions to α,β-dihalogenovinyl sulfones,
NUCLEOPHILIC REACTIONS AT A VINYL CENTER. XIII. REACTION OF β,β-DIBROMOVINYL PHENYL SULFONE WITH SODIUM IODIDE AND THE REACTIVITY OF β,β-DIIODOVINYL PHENYL SULFONE
Shainyan, B. A.,Mirskova, A. N.
, p. 1989 - 1993 (2007/10/02)
β-Bromo-β-iodovinyl phenyl sulfone and β,β-diiodovinyl phenyl sulfone were obtained by the reaction of β,β-dibromovinyl phenyl sulfone with sodium iodide in acetone.The reactivity of β,β-diiodovinyl phenyl sulfone in reactions with sodium methoxide and thiophenolates was studied.A comparison was made of the relative reactivities of the various β,β-dihalogenovinyl sulfones (Hlg = Cl, Br, I) in nucleophilic vinylic substitution within the scope of the elimination-addition and direct substitution mechanisms.
