106994-75-6Relevant 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
A NOVEL METHOD FOR CYCLOPENTANNELATION USING REGIOSELECTIVE ACYLATION OF ALLYLIC SULFIDES VIA α-SILYL INTERMEDIATES
Hiroi, Kunio,Sato, Hiroyasu,Kotsuji, Kumiko
, p. 743 - 746 (2007/10/02)
An aluminum chloride-catalyzed reaction of 1-(phenylthiotrimethylsilylmethyl)cyclohexene, readily obtainable from cyclohexanone, with acid chlorides in dichloromethane underwent a regioselective acylation at the γ-position of the allylic system to give γ-acyl enol thioethers in good yields.Heating of these enol thioethers with an equimolar amount of p-toluenesulfonic acid produced 2-cyclopentenone derivatives.This novel method for cyclopentannelation provides a new entry to 2-cyclopentenone ring systems.
