78905-22-3Relevant academic research and scientific papers
Acid-Catalyzed Regioselective Acylation of α-Silylallylic Sulfides and Its Application to a Novel Cyclopentannelation and Furan Annelation
Hiroi, Kunio,Sato, Hiroyasu,Chen, Lih-Ming,Kotsuji, Kumiko
, p. 1413 - 1426 (2007/10/02)
Introduction of a silyl group at the α-position of allylic sulfides, followed by the aluminum chloride-catalyzed reaction of the resulting α-silylallylic sulfides with acid chlorides resulted in regioselective acylation at the γ-position of the allylic system to give γ-acylated vinylic sulfides, chemically equivalent to 1,4-dicarbonyl compounds.Heating of the products in refluxing benzene with an equimolar amount of p-toluenesulfonic acid produced 2-cyclopentanone derivatives.Treatment of the acylated products with an equimolar amount of concentrated sulfuric acid gave α-phenylthiofuran derivatives.These procedures provide a novel method for cyclopentannelation and furan annelation.Keywords - α-silylallylic sulfide; acid chloride; aluminum chloride; acid-catalyzed acylation; vinylic sulfide; 2-cyclopentanone; α-phenylthiofuran; furan; cyclopentannelation; furan annelation
