78872-18-1Relevant academic research and scientific papers
Radical intermediates in the Zn-promoted Barbier-type alkylation of diphenyl diselenide in aqueous medium
Dos Anjos, Jose Ayron Lira,Bieber, Lothar Wilhelm
, p. 6492 - 6494,3 (2012/12/12)
The zinc promoted Barbier-type reaction of alkyl halides and diphenyl diselenide in aqueous medium leads to high yields of mixed selenides even in acidic medium. Especially the efficient formation of t-butylphenylselenide cannot be explained by nucleophil
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.
SH2 Reactions of Diphenyl Diselenide; Preparation and Reactions of Bridgehead Selenides
Perkins, M. John,Turner, Eric S.
, p. 139 - 140 (2007/10/02)
For the SH2 process R* + PhSeSePh -> PhSeR + PhSe*, k = ca. 5 * 107 l mol-1 s-1 at 80 deg C in benzene when R is primary alkyl; with 1-adamantyl radicals this SH2 displacement affords a route to 1-adamantyl phenyl selenide which, on oxidation and pyrolysis of the resultant selenoxide, gives adamantan-1-ol; in contrast the selenoxide from bicyclononan-1-yl phenyl selenide decomposes via bicyclonon-1-ene.
