96540-38-4

Upstream product

• 136495-07-3 2-Bromo-3,3-bis-methylsulfanyl-acrylic acid (E)-3-phenyl-allyl ester 
• 143158-73-0 cinnamyl 3,3-bis(methylthio)-2-propenoate 
• 146743-99-9 cinnamyl ethyl α-diazomalonate 
• 96540-32-8 1-ethoxycarbonyl-3-oxa-2-oxo-6-phenylbicyclo<3.1.0>hexane 
• 96540-63-5 cinnamyl ethyl malonate 
• 96540-34-0 3-ethoxycarbonyl-4-(1-iodobenzyl)-4,5-dihydrofuran-2(3H)-one 
• 64-17-5 ethanol 
• 136495-13-1 4-Benzyl-3-(bis-methylsulfanyl-methylene)-dihydro-furan-2-one 

Downstream Products

• 22530-98-9 4-benzyl-dihydro-furan-2-one 
• 16720-76-6 4-(phenylmethyl)-2(5H)-furanone 
• 96540-46-4 4-benzyl-3-phenylthio-4,5-dihydrofuran-2(3H)-one 
• 96540-49-7 4-benzyl-3-phenylsulfinyl-4,5-dihydrofuran-2(3H)-one 
• 96540-42-0 3-carbonyl-4-benzyl-4,5-dihydrofuran-2(3H)-one 

Relevant academic research and scientific papers

Intramolecular Radical Cyclization of Ketene Dithioacetals

A novel intramolecular ketene radical cyclization was described.Treatment of α-bromo-β-alkoxycarbonyl- and α-bromo-β-oxoketene dithioacetals with tributyltin hydride and AIBN gave lactones and cyclic ketones bearing bis(methylthio)methylene substituent at α-position in moderate yields.Tandem radical cyclization of ketene radical synthons were also carried out.

Synthesis of 4-Alkyl-2(5H)-furanones

An alternative method for the synthesis of 4-alkyl-2(5H)-furanones is described.Intramolecular carbene addition reaction of α-diazo compounds (4) in the presence of rhodium acetate or copper acetylacetonate furnished the bicyclic compounds (5), which were subjected to cyclopropane ring-opening reaction to give the 4-alkyl-4,5-dihydrofuran-2(3H)-ones (6) regioselectively.These compounds (6) were further converted into 4-alkyl-2(5H)-furanones (14) in several steps.Keywords - carbene; intramolecular addition; butenolide; cyclopropanation; ring-opening reaction