ON CARBONYL PARTICIPATION IN THE SOLVOLYSES OF α-KETO MESYLATES

Article abstract of DOI:10.1016/S0040-4039(00)61934-2

α-amido mesylates generally solvolyze giving α-keto cations, bypassing cyclic ions derived from carbonyl (k_Δ) participation.A possible exception is the N,N-dimethylamido mesylate derived from (S)-mandelic acid in trifluoroacetic acid which gives a small amount (9percent) of retained product.