Dianion of sulfinylacetone as a synthetic equivalent of beta-enolate of propionic acid: a novel synthesis of carboxylic acids from alkyl halides with three-carbon elongation.
The reaction of the dianion of phenylsulfinylacetone with alkyl halides afforded beta-keto sulfoxides, which were first chlorinated with hexachloroethane and then treated successively with KH and t-BuLi to give carboxylic acids in three-steps in moderate overall yields from the alkyl halides. This procedure affords a good method for a synthesis of carboxylic acids from alkyl halides with three-carbon elongation.
Satoh
Tsuyoshi
T
Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Tokyo, Japan. tsatoh@ch.kagu.tus.ac.jp
Imai
Kentaro
K
D000096:Acetone / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis*; D005227:Fatty Acids / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D011422:Propionates / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013441:Sulfinic Acids / Q000737:chemistry*
D002264:Carboxylic Acids; D005227:Fatty Acids; D007202:Indicators and Reagents; D011422:Propionates; D013441:Sulfinic Acids; D000096:Acetone; C016173:undecanoic acid