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On carbonyl participation in solvolyses of α-keto mesylates

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
26
Issue
7
Identifiers
DOI: 10.1016/s0040-4039(00)61934-2

Abstract

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

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