1189376-41-7Relevant articles and documents
Synthesis of cyclic hydroxamic acids through -NOH insertion of ketones
Banerjee, Ranjan,Bruce King
, p. 4580 - 4583 (2009)
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.
