Synthesis of Cyclic Allylic Sulphides (Ring Sizes 5-15) via Phenylthio Participation
Dehydration of β-phenylthio alcohols occurs with PhS participation unless stereochemistry prevents it.Without PhS participation, mixtures of allylic and vinylic sulphides are formed, but with PhS participation routes to three families of cyclic allylic su
Hannaby, Malcolm,Warren, Stuart
p. 303 - 311
(2007/10/02)
Acid-Catalyzed Regioselective Acylation of α-Silylallylic Sulfides and Its Application to a Novel Cyclopentannelation and Furan Annelation
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
DEHYDRATION OF ALCOHOLS WITH AN ADJACENT PHENYLTHIO (PhS) GROUP
Rings produce particular constraints not experienced by acyclic systems.We have investigated how the change in conformational and steric factors caused by varying the ring size affects a reaction within cyclic systems.
Hannaby, Malcolm,Warren, Stuart
p. 3133 - 3136
(2007/10/02)
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