102104-39-2Relevant academic research and scientific papers
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.
α,β-Epoxy Sulfoxides as Useful Intermediates in Organic Synthesis. II. A Novel Synthesis of α-Sulfenylated Ketones and α-Sulfenylated Aldehydes from α,β-Epoxy Sulfoxides
Satoh, Tsuyoshi,Kumagawa, Takumi,Yamakawa, Koji
, p. 2849 - 2854 (2007/10/02)
Treatment of α,β-epoxy sulfoxides, prepared from 1-chloroalkyl phenyl sulfoxides and carbonyl compounds, with various kinds of alkane- or arenethiolates afforded α-sulfenylated ketones in good yields.This method also offered a novel procedure for a synthe
α,β-Epoxy Sulfoxides as Useful Intermediates in Organic Synthesis. I. A Novel Synthesis of Dialkyl Ketones and a Synthesis of Aldehydes from Ketones by One Carbon Elongation
Satoh, Tsuyoshi,Kaneko, Youhei,Izawa, Takao,Sakata, Kiichi,Yamakawa, Koji
, p. 1983 - 1990 (2007/10/02)
Treatment of α,β-epoxy sulfoxides, prepared from 1-chloroalkyl phenyl sulfoxides with ketones or aldehydes, with sodium benzeneselenolate gives dialkyl ketones or aldehydes in good yields under mild conditions.The mechanism of this reaction and an application of this process to a formal total synthesis of dihydrojasmone are described.
