106262-64-0Relevant academic research and scientific papers
α,β-Epoxy Sulfoxides as Useful Intermediates in Organic Synthesis. X. An Improved Synthesis of α,β-Unsaturated Carbonyl Compounds from Carbonyl Compounds with Carbon Homologation through α,β-Epoxy Sulfoxides
Satoh, Tsuyoshi,Itoh, Masayuki,Ohara, Teruhiko,Yamakawa, Koji
, p. 1839 - 1846 (2007/10/02)
Treatment of the α,β-epoxy sulfoxides derived from ketones and chloromethyl phenyl sulfoxide or 1-chloroalkyl phenyl sulfoxides with lithium perchlorate in the presence of tributylphosphine oxide in toluene at 110 deg C for about 1-3 h gave α,β-unsaturated aldehydes or α,β-unsaturated ketones in high yields.In contrast to these results, the α,β-epoxy sulfoxides derived from aldehydes did not give the desired α,β-unsaturated ketones.In this case, a sequential treatment of the α,β-epoxy sulfoxides with benzenethiolate and m-chloroperbenzoic acid afforded α-phenylsulfinylated ketones, which were heated in toluene at 110 deg C to give the desired enones in good overall yields.The oxidation of the α,β-unsaturated aldehydes obtained by this method gave α,β-unsaturated carboxylic acids in high yields.These procedures afforded a new method for the synthesis of α,β-unsaturated carbonyl compounds, including α,β-unsaturated esters, from carbonyl compounds with carbon homologation.
Stereospecific Desulfinylation of α,β-Epoxy Sulfoxides with Butyllithium. A New Synthesis of Epoxides and Allylic Alcohols from Carbonyl Compounds
Satoh, Tsuyoshi,Kaneko, Youhei,Yamakawa, Koji
, p. 2463 - 2470 (2007/10/02)
Desulfinylation of α,β-epoxysulfoxides, easily prepared from carbonyl compounds and 1-chloroalkyl phenyl sulfoxide, with 1 equivalent of butyllithium at low temperature gave epoxides in good yields.The similar α,β-epoxy sulfoxides having an arylmethyl gro
