An Update of the Rules for Pyranoside Sulfonate Displacement

Karl J. Hale, Leslie Hough, Soraya Manaviazar, Andrew Calabrese

Research output: Contribution to journalLetterpeer-review

49 Citations (Scopus)


The original 1967 Richardson–Hough rules for predicting SN2 displacement viability in carbohydrate sulfonate derivatives with external nucleophiles have now been updated. Not only do the original rules still hold, but the newly updated rules rationalize why O-triflates (trifluoromethanesulfonate esters) frequently allow many seemingly “disallowed” pyranosidic nucleophilic substitutions to proceed. The new guidelines, which are based on three decades of experimental evidence, allow the feasibility of many pyranosidic O-triflate SN2 displacements to be gauged beforehand.
Original languageEnglish
Pages (from-to)4838-4841
Number of pages4
JournalOrganic Letters
Issue number18
Early online date12 Sept 2014
Publication statusPublished - 2014


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