Synthesis of cyclic hydroxamic acids through -NOH insertion of ketones.
Treatment of cyclobutanone or cyclopentanone with N-hydroxybenzenesulfonamide under basic conditions yields the ring-expanded cyclic hydroxamic acid in 18-69% yield. Reactions of substituted cyclobutanones give ring expanded products where the -NOH group regio- and stereoselectively inserts to the more substituted position. This expansion likely proceeds through a mechanism that includes addition of the N-anion of N-hydroxybenzenesulfonamide to the ketone and a C-nitroso intermediate that rearranges to the final product.
Banerjee
Ranjan
R
Department of Chemistry, Salem Hall, Box 7486, Wake Forest University, Winston-Salem, North Carolina 27109, USA.
King
S Bruce
SB
D018360:Crystallography, X-Ray; D006877:Hydroxamic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D009589:Nitrogen Oxides / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D006877:Hydroxamic Acids; D007659:Ketones; D009589:Nitrogen Oxides; C039900:nitroxyl