121033-27-0Relevant articles and documents
Do the electronic effects of sulfur indeed control the π-selectivity of γ-sulfenyl enones? An investigation
Yadav, Veejendra K.,Babu, K. Ganesh,Parvez, Masood
, p. 3866 - 3874 (2007/10/03)
The electronic effects of sulfur in γ-sulfenyl enones are not transmitted to the carbonyl carbon through the π bond as reported previously. The diastereoselectivity is rather controlled by a combination of several other factors. The steric effects arising
Electroinitiated Oxygenation of Alkenyl Sulfides and Alkynes in the Presence of Thiophenol
Yoshida, Jun-ichi,Nakatani, Shogo,Isoe, Sachihiko
, p. 4855 - 4865 (2007/10/02)
Electrolysis of alkenyl sulfides in the presence of thiophenol with bubbling of molecular oxygen gave the corresponding α-(phenylthio) carbonyl compounds with the consumption of a catalytic amount of electricity.An electroinitiated radical chain mechanism has been proposed.The reaction also took place without electrochemical initiation, but much (5-50 times) longer reaction time was required for the completion of the reaction.The potential utility of the present reaction in organic synthesis is demonstrated by the net 1,2-transposition of a phenylthio group and a carbonyl group.The electroinitiated oxygenation of ketene dithioacetals also proceeded smoothly to give the corresponding α-(phenylthio) thiol esters.It was also found that the electroinitiated oxygenation of alkynes in the presence of thiophenol gave α-(phenylthio) carbonyl compounds.A mechanism involving the initial formation of alkenyl sulfides has been proposed.
