89761-22-8Relevant academic research and scientific papers
Aldehyde to Ketone Homologation Enabled by Improved Access to Thioalkyl Phosphonium Salts
Fragis, Meghan,Deobald, Jackson L.,Dharavath, Srinivas,Scott, Jeffrey,Magolan, Jakob
supporting information, p. 4548 - 4552 (2021/06/28)
Phosphines were previously unusable as Pummerer-type nucleophiles due to competing redox chemistry with sulfoxides. Here we circumvent this problem to achieve a formal phosphine Pummerer reaction that offers thioalkyl phosphonium salts that, in turn, give rise to diverse vinyl sulfides via Wittig olefinations. Thirty vinyl sulfides are thus prepared from (alkylthioalkyl)triphenyl phosphonium salts and aldehydes. The hydrolysis of these vinyl sulfides offers an efficient and versatile two-step one-carbon homologation of aldehydes to ketones.
Mg-promoted stereoselective desulfonation of β-arylvinyl sulfone derivatives
Nishiguchi, Ikuzo,Matsumoto, Takeshi,Kuwahara, Takeshi,Kyoda, Makoto,Maekawa, Hirofumi
, p. 478 - 479 (2007/10/03)
β-Arylvinyl ρ-tolylsulfones, easily prepared from base-catalyzed condensation of aromatic aldehydes with a variety of ρ-tolylsulfones, were efficiently transformed to the corresponding (E)-β-substituted aromatic olefins in a stereoselective manner through Mg-promoted reduction. The reaction may be initiated through electron transfer from Mg metal to the vinyl sulfones to give the corresponding anionic species followed by stereoselective elimination of a sulfonyl group.
Electrolytic Reduction of 1-Methylsulfinyl-1-methylthio-1-alkenes at Mercury Electrode in Nonaqueous Media
Kunugi, Akira,Abe, Kyo,Hagi, Toshio,Hirai, Taketsugu
, p. 2009 - 2010 (2007/10/02)
In the electrolytic reduction of organic sulfur compounds of general formula RCH=C(SMe)S(O)Me, the substrates with R=aryl are much easier to reduce than those with R=alkyl, and the former substrates afford the desulfinylated compounds, E-isomers of RCH=CH
ELECTROLYTIC REDUCTION OF 1-METHYSULFINYL-1-METHYLTHIO-2-ARYLETHENES AT MERCURY AND PLATINUM ELECTRODES IN ACETONITRILE
Kunugi, Akira,Abe, Kyo
, p. 159 - 162 (2007/10/02)
The electrolytic reduction of 1-methylsulfinyl-1-methylthio-2-arylethenes involves a cleavage of one carbon-sulfur bond, resulting in formation of E-1-methylthio-2-arylethenes in good yields, but not Z-isomers, in the presence of excess phenol as a proton donor.
