55705-17-4Relevant academic research and scientific papers
One-pot synthesis of α-phenylsulfinyl ketones by reaction of phenyl benzenethiosulfinate with enolate anions, and synthesis of sulfoxides and sulfides by its reaction with Grignard reagents
Fakhry, Jerome,Grayson, David H.
, p. 556 - 563 (2017/12/28)
Phenyl benzenethiosulfinate reacts with enolate anions derived from ketones to give α-phenylsulfinyl ketones directly, together with minor amounts of α-phenylsulfanyl ketones. These are easily separated by forming the water-soluble sodium salts of the sulfinyl compounds. Grignard reagents also react with phenyl benzenethiosulfinate, to give mixtures of sulfoxides and sulfides.
α-Benzoyloxylation of β-keto sulfides at ambient temperature
Piras, Enrico,Secci, Francesco,Caboni, Pierluigi,Casula, Maria Francesca,Frongia, Angelo
, p. 49215 - 49219 (2017/11/03)
A facile and efficient protocol for the α-benzoyloxylation of β-keto sulfides is presented. This methodology provides a step-economical, mild and practical access to highly functionalized α-O-benzoyloxy substituted β-keto sulfides, including those with quaternary carbons, which are not easily obtained through currently available methods.
The formation of bicyclo[n.2.0]alkan-1-ols from the reaction of the lithium enolates of simple ketones and phenyl vinyl sulfoxide
Loughlin, Wendy A.,McCleary, Michelle A.
, p. 1347 - 1353 (2007/10/03)
The enolates generated from cyclopentanone, cycloheptanone or cyclooctanone and LDA at -78°C in THF react with (±)-phenyl vinyl sulfoxide under controlled conditions of temperature, reaction time, and concentration. Upon oxidation with MCPBA of the produc
Generation of the α-Sulfinyl Carbenoid from α-Chloro Sulfoxides: A New Method for One-Carbon Homologation of Ketones to α-Sulfinyl Ketones
Satoh, Tsuyoshi,Hayashi, Yasumasa,Mizu, Yasuhiro,Yamakawa, Koji
, p. 1412 - 1418 (2007/10/02)
Treatment of 1-chloroalkyl phenyl sulfoxides with a base gave carbenoids rather than free carbenes.The carbenoids were successfully used in a new method for homologation of ketones to α-sulfinyl ketones.Treatment of the carbanion of chloromethyl phenyl sulfoxide with ketones gave the adducts, α-chloro β-hydroxy sulfoxides, in nearly quantitative yields. the adducts were treated with excess lithium diisopropylamide to give one-carbon homologated α-sulfinyl ketones via α-sulfinyl β-oxido carbenoids in moderate to good yields.This type of reaction was found not to occur with the corresponding sulfones.
α-Sulfinyl carbenoid: One-carbon homologation of ketones to α-sulfinyl ketones using chloromethyl phenyl sulfoxide
Satoh, Tsuyoshi,Hayashi, Yasumasa,Mizu, Yasuhiro,Yamakawa, Koji
, p. 7181 - 7184 (2007/10/02)
Addition of the carbanion of chloromethyl phenyl sulfoxide to ketones gave the adducts, which were treated with lithium diisopropylamide to afford one-carbon homologated α-sulfinyl ketones via α-sulfinyl carbenoids in moderate to high yields.
