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Corey–Seebach Reaction
The Corey–Seebach reaction, or Seebach Umpolung is a name reaction of organic chemistry that allows for acylation by converting aldehydes into lithiated dithiane#1,3-Dithianes, 1,3-dithianes. The lithiated 1,3-dithianes serves as an acyl anion equivalent, undergoing alkylation with electrophiles. The reaction is of pedagogical value, but it is cumbersome, so it is not widely used. Implementation The aldehyde is first converted into a dithiane, usually with 1,3-propanedithiol. The resulting 1,3-dithiane is then lithiated with the use of N-butyllithium, butyllithium. The 2-lithio-1,3-dithiane reacts with electrophiles to give a 2-alkyl-1,3-dithiane. Finally, the 2-alkyl-1,3-dithiane can be converted to a carbonyl by hydrolysis, usually with the use of mercury(II) oxide. Alternatively the 2-alkyl-1,3-dithiane can be reduced to an alkane. : Scope The lithiated 1,3-dithiane can react with alkyl halides, epoxides, ketones, acyl halides, and iminium salts, which after hydrolysis o ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Elias James Corey
Elias James Corey (born July 12, 1928) is an American organic chemistry, organic chemist. In 1990, he won the Nobel Prize in Chemistry "for his development of the theory and methodology of organic synthesis", specifically retrosynthetic analysis. Regarded by many as one of the greatest living chemists, he has developed numerous synthetic reagents, methodologies and total syntheses and has advanced the science of organic synthesis considerably. Biography E.J. Corey (the surname was anglicized from Levantine Arabic ''Khoury'', meaning ''priest'') was born to Lebanese Greek Orthodox Christians, Lebanese Greek Orthodox Christian immigrants Fatima (née Hasham) and Elias Corey in Methuen, Massachusetts, north of Boston. His mother changed his name from William to "Elias" to honor his father, who died eighteen months after Corey's birth. His widowed mother, brother, two sisters, aunt and uncle all lived together in a spacious house, struggling through the Great Depression. As a young b ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
