title: Probing the hydrolytic reactivity of 2-difluoromethyl pyrroles.
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.
authors.affiliation: Department of Chemistry, Dalhousie University, P.O. Box 15000, Halifax, NS B3H 4R2, Canada. Alison.Thompson@dal.ca.
authors.forename: Jennifer A
authors.initials: JA
authors.lastname: Melanson
authors.affiliation: Department of Chemistry, Dalhousie University, P.O. Box 15000, Halifax, NS B3H 4R2, Canada. Alison.Thompson@dal.ca.
authors.forename: Carlotta
authors.initials: C
authors.lastname: Figliola
authors.affiliation: Department of Chemistry, Dalhousie University, P.O. Box 15000, Halifax, NS B3H 4R2, Canada. Alison.Thompson@dal.ca.
authors.forename: Deborah A
authors.initials: DA
authors.lastname: Smithen
authors.affiliation: Department of Chemistry, Dalhousie University, P.O. Box 15000, Halifax, NS B3H 4R2, Canada. Alison.Thompson@dal.ca.
authors.forename: Aleksandra K
authors.initials: AK
authors.lastname: Kajetanowicz
authors.affiliation: Department of Chemistry, Dalhousie University, P.O. Box 15000, Halifax, NS B3H 4R2, Canada. Alison.Thompson@dal.ca.
authors.forename: Alison
authors.initials: A
authors.lastname: Thompson