Probing the hydrolytic reactivity of 2-difluoromethyl pyrroles
Jennifer A Melanson1, Carlotta Figliola1, Deborah A Smithen1
1Department of Chemistry, Dalhousie University, P.O. Box 15000, Halifax, NS B3H 4R2, Canada. Alison.Thompson@dal.ca.
Abstract:
α-Difluoromethyl pyrroles were found to be stable while N-protected with an electron-withdrawing group. Due to the propensity of pyrroles to access azafulvenium-like intermediates, the C-F bonds of an α-difluoromethyl substituent are labile under hydrolytic conditions. The presence of certain electron-withdrawing substituents about the pyrrolic ring can accelerate this process, as determined through a kinetic comparison of the deprotection and subsequent hydrolysis reactions of N-protected β-aryl α-difluoromethyl pyrroles.
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