80351-84-4Relevant articles and documents
NOVEL REARRANGEMENTS OF α-N-ALKYLAMIDO-SUBSTITUTED SULFIDES AND SULFONES
Ishikawa, Yoshiharu,Kurebayashi, Yasuo,Suzuki, Kunio,Terao, Yoshiyasu,Sekiya, Minoru
, p. 2496 - 2502 (2007/10/02)
The present paper describes novel rearrangements of α-N-alkylamido-substituted sulfides and sulfones promoted by strong bases such as NaH, lithium diisopropylamide and butyllithium, where the alkyl group linked to the sulfur migrates to the amide carbonyl carbon to give the corresponding ketones.The reactions are established as intramolecular rearrangements, and the mechanism is discussed.Keywords: - alkyl (N-alkylamido)methyl sulfide; alkyl (N-alkylamido)methyl sulfone; alkyl α-(N-alkylamido)benzyl sulfide; intramolecular rearrangement; sodium hydride; lithium diisopropylamide; butyllithium