Probing the hydrolytic reactivity of 2-difluoromethyl pyrroles. Issue 1 (14th November 2016)

• Record Type: Journal Article
• Authors: Melanson, Jennifer A.; Figliola, Carlotta; Smithen, Deborah A.; Kajetanowicz, Aleksandra K.; Thompson, Alison
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 1(2017)
• Page Start: 144
• Page End: 152
• Publication Date: 2016-11-14
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob01441k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : α-Difluoromethyl pyrroles were found to be stable while N -protected with an electron-withdrawing group. 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.