18893-63-5Relevant articles and documents
DTBB-catalysed lithiation of 1,2-bis(phenylsulfanyl)ethene: Does 1-lithio-2-phenylsulfanylethene really exist?
Gómez, Cecilia,Maciá, Beatriz,Yus, Miguel
, p. 9325 - 9330 (2007/10/03)
The reaction of (Z)- or (E)-1,2-bis(phenylsulfanyl)ethene (1) with an excess of lithium and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 2.5 mol%) in the presence of a carbonyl compound as electrophile (Barbier conditions) in THF at -78°C leads, after hydrolysis with water at temperatures ranging between -78°C and rt, to a mixture of the corresponding (Z/E)-unsaturated 1,4-diols 2, the diastereomers ratio being independent of the stereochemistry of the starting materials. Allylic alcohols 3 are the main by-products, resulting from a lithium-hydrogen exchange on some of the lithiated intermediates along the whole process. A mechanistic explanation for the observed behaviour is given.
Relative Reactivities of Various Sulfides, Selenides and Halides Towards SH2 Attack by Tributyltin Radicals
Beckwith, Athelstan L. J.,Pigou, Paul E.
, p. 77 - 87 (2007/10/02)
The order of reactivity towards SH2 attack by tributyltin radicals on various groups X in four different molecular environments (RCO2CH2X, RCH2OCH2X, XCH2CO2Et and RCH2X) has been found by competition experiments to be Br > PhSe > Cl > p-CNC6H4S > PhS > p-MeC6H4S > MeS.The mechanism of the reaction of chloromethyl phenyl sulfide with alkoxides is discussed.