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Paper | Special issue | Vol 99, No. 1, 2019, pp.484-501
Published online, 22nd November, 2018
DOI: 10.3987/COM-18-S(F)43
[Bis(trifluoroacetoxy)iodo]p-nitrobenzene and [Bis(trifluoroacetoxy)iodo]pentafluorobenzene as Lead Reagents for the Direct Ring Contraction of Lactams to Pyrrolidines

Samuel Aubert-Nicol, Nora Heinrich, Jean Lessard, and Claude Spino*

*Chemistry Department, University of Sherbrooke, 2500 Boul. Université, Sherbrooke, QC, J1K 2R1, Canada

Abstract

Two λ3iodanes, namely [bis(trifluoroacetoxy)iodo]p-nitrobenzene and [bis(trifluoroacetoxy)iodo]pentafluorobenzene, were used to effect the direct ring-contraction of lactams to pyrrolidines. Intense reaction optimization was necessary but only α,α-disubstituted lactams succumbed to our efforts thus far.