70910-88-2Relevant academic research and scientific papers
α,β-Epoxy Sulfoxides as Useful Intermediates in Organic Synthesis. IX. A Novel Synthesis of Alkyl Vinyl Ketones and Divinyl Ketones from Carbonyl Compounds and 1-Chloro-3-phenylthiopropyl Phenyl Sulfoxide as a Three-Carbon Homologating Agent
Satoh, Tsuyoshi,Kumagawa, Takumi,Sugimoto, Atsushi,Yamakawa, Koji
, p. 301 - 310 (2007/10/02)
The α,β-epoxy sulfoxides easily derived from carbonyl compounds and 1-chloro-3-phenylthiopropyl phenyl sulfoxide were treated with sodium benzeneselenolate to give β-phenylthio carbonyl compounds in excellent yields.The phenylthio group was oxidized to the sulfinyl group and was then treated with a base to afford alkyl vinyl ketones in quite good yields.This reaction presents a novel method for the preparation of alkyl vinyl ketones from carbonyl compounds by three-carbon homologation.The treatment of α,β-epoxy sulfoxides mentioned above with benzenethiolate gave α,β'-bis(phenylthio) ketones.The elimination of the both thio groups afforded divinyl ketones.
A NOVEL SYNTHESIS OF ALKYL VINYL KETONES AND DIVINYL KETONES FROM CARBONYL COMPOUNDS BY THREE-CARBON HOMOLOGATION
Satoh, Tsuyoshi,Kumagawa, Takumi,Yamakava, Koji
, p. 2471 - 2474 (2007/10/02)
Alkyl vinyl ketones and divinyl ketones are synthesized from carbonyl compounds and 1-chloro-3-phenylthiopropyl phenyl sulfoxide as a three-carbon homologating agent in good overall yileds.
