Sulfonylation-induced N- to O-acetyl migration in 2-acetamidoethanol derivatives.
The first example of sulfonylation-induced N- to O-acetyl migration of 2-acetamidoethanol derivatives is described. This type of reaction could happen with any 2-acetamidoethanol derivatives under typical sulfonylation conditions (TsCl or MsCl, pyridine) and might be a common side reaction of significance. Furthermore, the results reveal that 2-acetamidoethanol derivatives with a sterically encumbered hydroxyl group result in the migration products in high yields. The mechanism of the migration reaction is discussed.
Yamaguchi
Takao
T
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
Hesek
Dusan
D
Lee
Mijoon
M
Oliver
Allen G
AG
Mobashery
Shahriar
S
D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D000431:Ethanol / Q000031:analogs & derivatives* / Q000737:chemistry*; D015394:Molecular Structure; D013451:Sulfonic Acids / Q000737:chemistry*
D004952:Esters; D013451:Sulfonic Acids; D000431:Ethanol