95110-49-9Relevant articles and documents
A Novel Synthesis of Methylenecyclopropane Spiro-Linked with Cycloalkanes via a Cyclization of Allylic Epoxides and Its Application to a Synthesis of Fused 3-Methylfurans
Satoh, Tsuyoshi,Kawase, Yasushi,Yamakawa, Koji
, p. 1129 - 1135 (2007/10/02)
Ring closure of allylic epoxides derived from 1-chloroalkyl phenyl sulfoxides and cyclic ketones with lithium diisopropylamide (LDA) in 3-Exo-Tet mode gave spiro-linked methylenecyclopropanes having a hydroxyl group in good yields.Oxidation of these compounds gave ketones, which were then treated with p-toluenesulfonic acid in 1,4-dioxane or DMSO at 100 deg C to give fused 3-methylfurans in good overall yields.This procedure was applied to a synthesis of menthofuran from 4-methylcyclohexanone.
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.
