95110-74-0Relevant articles and documents
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.
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.
